N-bromobutanimide → 2-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol

HRID 2107560ノート

反応式

HRID 2107560 の反応式
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]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 709342,3-DihydrofuranHCID 2723790Thiourea

生成物 1

HCID 136371842-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  1. temperaturethe solution refluxed under a nitrogen atmosphere overnight
  2. extractionThe acidic solution is continuously extracted with ethyl acetate for 24 hours The ethyl acetate
  3. extractionextract
  4. extractioncontinuously extracted with ethyl acetate for 72 hours
  5. extractionThe ethyl acetate extract
  6. temperatureis cooled
  7. customThe hydrochloride salt oils out of solution and is crystallized from an ethanol-acetonitrile mixture

出典と根拠

ORDレコード
ord-b339928a557d43668c409bf95d978da6
出典データセット
uspto-grants-1990_06
特許番号
US04935424

反応ノート

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