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

HRID 1660806Notes

Reaction equation

HRID 1660806 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-64921269b6ec42f7b27cf4358480298f
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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