N-bromobutanimide → 2-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol
Reaction equation
Br[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].O1C=CCC1.[NH2:14][C:15](N)=[S:16]>O>[NH2:14][C:15]1[S:16][C:5]([CH2:4][CH2:3][OH:8])=[CH:6][N:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an ice cold suspension of 118.2 g of N-bromosuccinimide in 750 ml of water under a nitrogen atmosphere is added dropwise 75 ml of 2,3-dihydrofuran. The resulting solution is stirred at 0° C. for one hour. Thiourea, 50.5 g, is added and the solution refluxed under a nitrogen atmosphere overnight. The acidic solution is continuously extracted with ethyl acetate for 24 hours The ethyl acetate extract contains mostly succinimide. The aqueous phase is basified with concentrated ammonium hydroxide to a pH of 10-11 and continuously extracted with ethyl acetate for 72 hours. The ethyl acetate extract is cooled and acidified with ethereal hydrogen chloride. The hydrochloride salt oils out of solution and is crystallized from an ethanol-acetonitrile mixture to give 60.1 g of 2-amino-5-thiazoleethanol as the monohydrochloride salt; mp 125°-127° C. (lit. (a) mp 126°-127° C.) lit. (a) Farmaco. Ed. Sci., Vol. 41, pages 483-498 (1986).
Workup
- temperaturethe solution refluxed under a nitrogen atmosphere overnight
- extractionThe acidic solution is continuously extracted with ethyl acetate for 24 hours The ethyl acetate
- extractionextract
- extractioncontinuously extracted with ethyl acetate for 72 hours
- extractionThe ethyl acetate extract
- temperatureis cooled
- customThe hydrochloride salt oils out of solution and is crystallized from an ethanol-acetonitrile mixture
Sources & evidence
- ORD record
- ord-b339928a557d43668c409bf95d978da6
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04935424
Reaction notes
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