Benzoyl isothiocyanate → N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamide

HRID 712148노트

반응식

HRID 712148 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([Br:16])[CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][C:26]([NH:25][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[S:27])[CH:13]=[C:14]([Br:16])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 578136263-(Benzyloxy)-5-bromoaniline

생성물 1

HCID 57813640N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamide수율 85%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
40 °C

실험 절차

To a solution of 3-benzyloxy-5-bromo-aniline (480 g, 1.73 mol) in acetone (10 L) was added benzoylisothiocyanate (280 mL, 2.08 mol) at rt. After stirring the reaction mixture for 15 min, solid precipitated out and stirring was continued for 30 min at rt. After completion of reaction (by TLC), acetone was distilled off. Hexane (2 L) was added and again concentrated. To the concentrated solid was added hexane (4 L) heated to 40° C. for 30 min under stirring and the solid filtered. The solid was washed with hexane (2×2 L) to obtain the desired product (648 g, 85%).

후처리

  1. customsolid precipitated out
  2. stirringstirring
  3. waitwas continued for 30 min at rt
  4. customAfter completion of reaction (by TLC), acetone
  5. distillationwas distilled off
  6. additionHexane (2 L) was added
  7. concentrationagain concentrated
  8. additionTo the concentrated solid was added hexane (4 L)
  9. stirringunder stirring
  10. filtrationthe solid filtered
  11. washThe solid was washed with hexane (2×2 L)

출처 및 근거

ORD 기록
ord-42d1b256812e4f4bb9a9e690709e631a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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