Benzoic acid, 4-(acetyloxy)- → p-Acetoxybenzoyl chloride
Reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([O:10][C:11]1[CH:19]=[CH:18]C(C(O)=O)=[CH:13][CH:12]=1)(=[O:9])[CH3:8]>C(Cl)Cl.CN(C=O)C>[C:7]([O:10][C:11]1[CH:19]=[CH:18][C:1]([C:2]([Cl:4])=[O:3])=[CH:13][CH:12]=1)(=[O:9])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (0.35 ml) was added to a stirred suspension of 4-acetoxybenzoic acid (0.57 g) in methylene chloride (15 ml) which had been cooled to 0° C. DMF (2 drops) was added and the mixture was stirred at ambient temperature for 4 hours. The mixture was evaporated to give 4-acetoxybenzoyl chloride which was used without further purification. A mixture of the acid chloride so obtained, N-(3-amino-4-chlorophenyl)-4-cyanobenzamide (0.813 g) and pyridine (15 ml) was stirred and heated at 100° C. for 16 hours. The mixture was cooled to ambient temperature and poured into 2N aqueous hydrochloric acid solution (175 ml). The precipitate was isolated, washed with water and dried. The material so obtained was purified by column chromatography on silica using a 7:3 mixture of isohexane and ethyl acetate as eluent. There was thus obtained the title compound (0.74 g); m.p. 195-196° C.
Workup
- customThe mixture was evaporated
Sources & evidence
- ORD record
- ord-bf438f129d634d4c9cb247d55e48924b
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06465455B1
Reaction notes
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