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

HRID 1660806노트

반응식

HRID 1660806 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-64921269b6ec42f7b27cf4358480298f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030308B2

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