Benzoyl chloride → Isopropyl 5-benzamido-2-chloro-4-fluoro-benzoate

HRID 326339Notes

Reaction equation

HRID 326339 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[C:12]([F:24])=[CH:13][C:14]([Cl:23])=[C:15]([CH:22]=1)[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]>C(C(C)=O)C>[C:1]([NH:10][C:11]1[C:12]([F:24])=[CH:13][C:14]([Cl:23])=[C:15]([CH:22]=1)[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 13519894Propan-2-yl 5-amino-2-chloro-4-fluorobenzoate

Product 1

HCID 507314Isopropyl 5-benzamido-2-chloro-4-fluoro-benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of benzoyl chloride (2.94 g, 0.021 mole) and 1-methylethyl 5-amino-2-chloro-4-fluorobenzoate (4.62 g, 0.020 mole) in methyl ethyl ketone (50 ml) was stirred at room temperature for 3 days. Evaporation of the solvent and crystallization of the solid residue from ethyl ether gave colorless needles, m.p. 117°-119° C. (6 g, 90% yield).

Workup

  1. customEvaporation of the solvent and crystallization of the solid residue from ethyl ether
  2. customgave colorless needles, m.p. 117°-119° C. (6 g, 90% yield)

Sources & evidence

ORD record
ord-7b73076e500c4e2e99da51880a681630
Source dataset
uspto-grants-1993_12
Patent number
US05268389

Reaction notes

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