GB609803A - A process for the preparation of 2-methyl-2.3-di-halogen-tetrahydrofuranes and their conversion to vitamin b and the like - Google Patents
A process for the preparation of 2-methyl-2.3-di-halogen-tetrahydrofuranes and their conversion to vitamin b and the likeInfo
- Publication number
- GB609803A GB609803A GB4543/41A GB454341A GB609803A GB 609803 A GB609803 A GB 609803A GB 4543/41 A GB4543/41 A GB 4543/41A GB 454341 A GB454341 A GB 454341A GB 609803 A GB609803 A GB 609803A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aceto
- halogen
- vitamin
- methyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 229940088594 vitamin Drugs 0.000 title 1
- 229930003231 vitamin Natural products 0.000 title 1
- 235000013343 vitamin Nutrition 0.000 title 1
- 239000011782 vitamin Substances 0.000 title 1
- 150000003722 vitamin derivatives Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 3
- 229930003451 Vitamin B1 Natural products 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 229960003495 thiamine Drugs 0.000 abstract 2
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 239000011691 vitamin B1 Substances 0.000 abstract 2
- 235000010374 vitamin B1 Nutrition 0.000 abstract 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
Vitamin B1 is obtained by reacting, preferably in the presence of acid binding agents, 2-alkyl-4-amino - 5 - (thioformamido - alkyl) pyrimidines with 2-methyl-2 : 3-dihalogen-tetrahydrofuranes prepared by subjecting g - aceto - g - halogen - propyl alcohol, or its cyclic form, or an ether of the cyclic form such as an alkyl ether or its ether formed with g -aceto-g -halogen-propyl alcohol, or mixtures of them, or reaction mixtures containing any one of these compounds, to reagents which are generally used for substituting a hydroxyl by a halogen group. Preferably, the reaction is carried out in 90 per cent formic acid as the reaction medium. Suitable acid binding agents are pyridine and potassium formate. Detailed examples are given of the preparation of 2-methyl-2 : 3-dichloro-tetrahydrofurane by treating aceto-chloro-propyl alcohol with an aceto-chlorobutyrolactone with thionyl chloride, hydrogen chloride gas and hydrochloric acid. An additional example describes the preparation of Vitamin B1 using pyridine as the acid binding agent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU609803X | 1940-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB609803A true GB609803A (en) | 1948-10-07 |
Family
ID=10979734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4543/41A Expired GB609803A (en) | 1940-05-25 | 1941-04-04 | A process for the preparation of 2-methyl-2.3-di-halogen-tetrahydrofuranes and their conversion to vitamin b and the like |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB609803A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2678319A (en) * | 1952-02-20 | 1954-05-11 | Du Pont | Preparation of 2,3-dihalotetrahydro-2-methylfurans |
-
1941
- 1941-04-04 GB GB4543/41A patent/GB609803A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2678319A (en) * | 1952-02-20 | 1954-05-11 | Du Pont | Preparation of 2,3-dihalotetrahydro-2-methylfurans |
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