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

HRID 712148ノート

反応式

HRID 712148 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
40 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-42d1b256812e4f4bb9a9e690709e631a
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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