Benzocaine → Benzoic acid, 4-[(3-nitrobenzoyl)amino]-, ethyl ester

HRID 2241125Notes

Reaction equation

HRID 2241125 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.[N+:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([O-:22])=[O:21]>ClCCl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 711477Benzoic acid, 4-[(3-nitrobenzoyl)amino]-, ethyl esterYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-amino benzoic acid ethyl ester (1.95 g, 11.8 mmol) in dry dichloromethane (20.0 ml) was treated with triethylamine (1.31 g, 13.0 mmol) and cooled to 0° C. 3-Nitrobenzoyl chloride (2.00 g, 10.8 mmol) was added portion wise over 5 min. The mixture was stirred at 0° C. for 5 min, then at room temperature for 10 min. The reaction was quenched by addition of 20 ml of saturated NaHCO3. The organic phase was separated and filtered washing with dichloromethane. Drying of the solid under high vacuum yielded 4-(3-nitro-benzoylamino)-benzoic acid ethyl ester as a white solid (2.52 g, 74%), MS (ISP): m/e=315.1 (M+H+).

Workup

  1. waitat room temperature for 10 min
  2. customThe reaction was quenched by addition of 20 ml of saturated NaHCO3
  3. customThe organic phase was separated
  4. filtrationfiltered
  5. washwashing with dichloromethane
  6. customDrying of the solid under high vacuum

Sources & evidence

ORD record
ord-7d88f9a7214d4adab5634b2d28d71431
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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