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Benzyl chloroformate → 5,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-benzoimidazole-1-carboxylic acid benzyl ester

HRID 25498
ノート
印刷プレビュー

反応式

HRID 25498 の反応式
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CN(C)C=O>[CH2:29]([O:28][C:26]([N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[C:21]([Cl:22])=[CH:20][C:5]=2[N:6]=[C:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 225684155,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole

生成物 1

HCID 698015975,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-benzoimidazole-1-carboxylic acid benzyl ester収率 43.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dimethylformamide (25 mL) was added to 5,6-dichloro-2-(4-methoxy-3-nitro-phenyl)-1H-benzoimidazole (1.01 g, 3 mmol) from Step A. As the mixture stirred, sodium hydride (0.168 g, 4.2 mmol) was gradually added. After 3 hours, benzyl chloroformate (0.857 mL, 6 mmol) was added dropwise to the mixture. The reaction mixture was stirred overnight and then was partitioned between water (1,000 mL) and ethyl acetate (500 mL). The solvent was removed on the rotary evaporator and the residue triturated with 4:1 hexane:ethyl acetate to give the product (0.62 g), mp 212-214° C.

後処理

  1. stirringThe reaction mixture was stirred overnight
  2. customwas partitioned between water (1,000 mL) and ethyl acetate (500 mL)
  3. customThe solvent was removed on the rotary evaporator
  4. customthe residue triturated with 4:1 hexane

出典と根拠

ORDレコード
ord-209d0ea531274ba2a9f569c82703f6e2
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06858739B2

反応ノート

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