Triethylamine → N-(4-propylphenyl)-5-(4-cyanobenzamido)-2-methylbenzamide

HRID 1266209Notes

Reaction equation

HRID 1266209 reaction equation
[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:11]([C:13]1[CH:31]=[CH:30][C:16]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:29])=[C:24]([CH:28]=2)[C:25](Cl)=[O:26])=[O:18])=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:25](=[O:26])[C:24]2[CH:28]=[C:20]([NH:19][C:17](=[O:18])[C:16]3[CH:30]=[CH:31][C:13]([C:11]#[N:12])=[CH:14][CH:15]=3)[CH:21]=[CH:22][C:23]=2[CH3:29])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759084-PropylanilineHCID 226677745-(4-Cyanobenzamido)-2-methylbenzoyl chloride

Product 1

HCID 9800950N-(4-propylphenyl)-5-(4-cyanobenzamido)-2-methylbenzamideYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-n-Propylaniline (0.11 g) was added to a stirred suspension of 5-(4-cyanobenzamido)-2-methylbenzoyl chloride (0.224 g), triethylamine (0.21 ml) and methylene chloride (5 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.049 g); NMR Spectrum: (DMSOd6) 0.87 (t, 3H), 1.56 (m, 2H), 2.33 (s, 3H), 2.48 (m, 2H), 7.13 (d, 2H), 7.28 (d, 1H), 7.63 (m, 2H), 7.83 (m, 3H), 8.01 (d, 1H), 8.1 (m, 2H); Mass Spectrum: M+H+ 398.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography on silica using
  4. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-76de84a752254c0bbefe12b47c2de6d0
Source dataset
uspto-grants-2003_04
Patent number
US06548514B1

Reaction notes

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