Triethylamine → N-(4-Cyano-3-trifluoromethyl-phenyl)-2-methoxy-benzamide

HRID 2055910Notes

Reaction equation

HRID 2055910 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8](CCCCCCCCCCCCCCC)[C:4]=1[C:5](Cl)=[O:6].[NH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:29]=1.C(N(CC)CC)C>ClCCl>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([NH:27][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[CH:29][C:30]=1[C:36]([F:37])([F:38])[F:39])#[N:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 104524032-methoxy-6-pentadecyl-benzoyl Chloride

Product 1

HCID 10245431N-(4-Cyano-3-trifluoromethyl-phenyl)-2-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-6-pentadecyl-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-methoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

Sources & evidence

ORD record
ord-aa3592641f564578becc408ac5e9752d
Source dataset
uspto-grants-2008_02
Patent number
US07332629B2

Reaction notes

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