Benzoyl isothiocyanate → 1-Benzoyl-3-(5-bromo-3-(phenylthio)pyridin-2-yl)thiourea

HRID 1809554노트

반응식

HRID 1809554 반응식
[Br:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[C:16]([NH:24][C:25]([NH:8][C:5]1[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 459260645-Bromo-3-(phenylthio)pyridin-2-amine

생성물 1

HCID 866314871-Benzoyl-3-(5-bromo-3-(phenylthio)pyridin-2-yl)thiourea수율 95.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Bromo-3-(phenylthio)pyridin-2-amine (17 g, 60.5 mmol), benzoyl isothiocyanate (9.79 mL, 72.6 mmol), and THF (300 mL) were stirred at 40° C. overnight. The THF was concentrated to ˜1/2 volume and 9:1 hexanes:EtOAc (500 mL) added and precipitate filtered to afford the title compound (25.7 g, 95.7% yield).

후처리

  1. concentrationThe THF was concentrated to ˜1/2 volume and 9:1 hexanes
  2. additionEtOAc (500 mL) added
  3. filtrationprecipitate filtered

출처 및 근거

ORD 기록
ord-6a7b047ae9534c1797cea17951cef04c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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