Benzocaine → 4-(4-Benzyloxy-3-nitro-benzoylamino)benzoic acid ethyl ester

HRID 641288ノート

反応式

HRID 641288 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH2:29]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][C:38]=1[N+:46]([O-:48])=[O:47])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl.O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:37]([O:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:38]([N+:46]([O-:48])=[O:47])[CH:39]=2)=[CH:7][CH:6]=1)[CH3:2]

参加物

7

反応物 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 204542884-Benzyloxy-3-nitro-benzoyl chloride

生成物 1

HCID 667887614-(4-Benzyloxy-3-nitro-benzoylamino)benzoic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-amino-benzoic acid ethyl ester (17 g, 103 mmol) in dichloromethane (500 mL) and triethylamine (20.8 g, 28.5 mL, 206 mmol) was treated with dimethylaminopyridine (0.63 g, 5 mmol) and 4-benzyloxy-3-nitro-benzoyl chloride (30 g, 103 mmol). The mixture was stirred at room temperature overnight, while a thick white precipitate formed. The slurry was diluted with water (10 mL) and stirred vigorously, then filtered, washing with dichloromethane and water. The solid was dried under high vacuum to yield 4-(4-benzyloxy-3-nitro-benzoylamino)-benzoic acid ethyl ester as a white solid, 26.5 g (61%), MS (ISP): m/e=419.3 (M−H).

後処理

  1. customformed
  2. stirringstirred vigorously
  3. filtrationfiltered
  4. washwashing with dichloromethane and water
  5. customThe solid was dried under high vacuum

出典と根拠

ORDレコード
ord-3d6ae209d1424062b4cb6328de70b444
出典データセット
uspto-grants-2010_04
特許番号
US07696200B2

反応ノート

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