Hydrogen Bromide → N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide

HRID 425235노트

반응식

HRID 425235 반응식
[BrH:1].[OH:2][C@H:3]([CH2:14]O)[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7].C(OC(=O)C)(=O)C.CO>C(O)(=O)C>[Br:1][CH2:14][C@@H:3]([OH:2])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7]

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 7918Acetic AnhydrideHCID 99916905-Chloro-N-((S)-2,3-dihydroxypropyl)thiophene-2-carboxamide

생성물 1

HCID 10108741N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
62.5 °C

실험 절차

301.7 ml of a 33% solution of hydrobromic acid in acetic acid are added to a suspension of 100 g of N-((S)-2,3-dihydroxypropyl)-5-chlorothiophene-2-carboxamide (VIII) in 250 ml of glacial acetic acid at from 21 to 26° C. over a period of 30 minutes. Subsequently, 40 ml of acetic anhydride are added and the reaction mixture is stirred at from 60 to 65° C. for three hours. At 20 to 25° C., 960 ml of methanol are then added over a period of 30 minutes. The reaction mixture is stirred under reflux for 2.5 hours and then overnight at from 20 to 25° C. For workup, the solvents are distilled off under reduced pressure at approx. 95 mbar. The remaining suspension is admixed with 50 ml of 1-butanol and 350 ml of water. The precipitated product is filtered off with suction, washed with water and dried.

후처리

  1. stirringThe reaction mixture is stirred
  2. temperatureunder reflux for 2.5 hours
  3. customovernight
  4. customat from 20 to 25° C
  5. distillationFor workup, the solvents are distilled off under reduced pressure at approx. 95 mbar
  6. filtrationThe precipitated product is filtered off with suction
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-2cc01475d2b741888dc6133267712869
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106192B2

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