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Triethylamine → 2-Methoxy-n-(4-nitro-3-trifluoromethyl-phenyl)-6-pentadecyl-benzamide

HRID 2055913
Notes
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Reaction equation

HRID 2055913 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=1[C:5](Cl)=[O:6].[NH2:27][C:28]1[CH:29]=[CH:30][C:31]([N+:38]([O-:40])=[O:39])=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=1[C:5]([NH:27][C:28]1[CH:29]=[CH:30][C:31]([N+:38]([O-:40])=[O:39])=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=1)=[O:6]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 949554-Nitro-3-(trifluoromethyl)anilineHCID 104524032-methoxy-6-pentadecyl-benzoyl Chloride

Product 1

HCID 684536612-Methoxy-n-(4-nitro-3-trifluoromethyl-phenyl)-6-pentadecyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-6-pentadecyl-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Methoxy-N-(4-nitro-3-trifluromethyl-phenyl)-6-pentadecyl-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-1bb876f6dff443398b210610d4a2f0b1
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07332629B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes