Water → [4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester

HRID 605265

反応式

HRID 605265 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[C:20]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[OH-].[K+].O>CS(C)=O>[C:23]([O:22][C:20](=[O:21])[NH:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:32][CH:33]=1)([CH3:26])([CH3:24])[CH3:25]

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2756771N-Boc-4-hydroxyanilineHCID 3535228N-(4-fluoro-3-nitrophenyl)benzamide

生成物 1

HCID 67040356[4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester収率 93.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of N-(4-fluoro-3-nitrophenyl)benzamide (1.00 g, 3.8 mmol), N-Boc-4-hydroxyaniline (0.83 g, 3.8 mmol) and 85% KOH (0.51 g, 7.7 mmol) in DMSO (20 mL) was heated at 80° C. for 1 hour, and then poured into H2O (100 ml) under stirring. The resulting oily crystal was extracted with EtOAc. The extract was washed with H2O (3 times) and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound, which was purified by washing with i-Pr2O to give the desired compound as yellow crystals (1.59 g, 92%).

後処理

  1. extractionThe resulting oily crystal was extracted with EtOAc
  2. washThe extract was washed with H2O (3 times) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound, which
  7. customwas purified
  8. washby washing with i-Pr2O

出典と根拠

ORDレコード
ord-0346ac4040c94a799838694124054c87
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

関連ノート

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