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

HRID 2353804Notes

Reaction equation

HRID 2353804 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-trifluoromethyl 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-3be673c561e74ad988d27e8cf3e2da02
Source dataset
uspto-grants-2010_07
Patent number
US07750047B2

Reaction notes

Loading…