Triethylamine → 3-(4-carboxybenzamido)-N-(3-dimethylaminophenyl)-4-methylbenzamide

HRID 2415705Notes

Reaction equation

HRID 2415705 reaction equation
C(N(CC)CC)C.C[O:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)=[O:11].[NH2:21][C:22]1[CH:23]=[C:24]([CH:37]=[CH:38][C:39]=1[CH3:40])[C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH3:36])[CH3:35])[CH:29]=1)=[O:26]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:21][C:22]2[CH:23]=[C:24]([CH:37]=[CH:38][C:39]=2[CH3:40])[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH3:36])[CH3:35])[CH:29]=2)=[O:26])=[O:17])=[CH:14][CH:13]=1)([OH:9])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 226361113-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide

Product 1

HCID 98882023-(4-carboxybenzamido)-N-(3-dimethylaminophenyl)-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.26 ml) was added to a stirred mixture of 4-methoxycarbonylbenzoyl chloride (0.221 g), 4-dimethylaminopyridine (0.01 g), 3-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide (0.2 g) and methylene chloride (10 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with methylene chloride and washed with a saturated aqueous sodium bicarbonate solution and with a saturated aqueous sodium chloride solution. The organic solution was dried over magnesium sulphate and evaporated. The residue was triturated under isohexane. The resultant solid was isolated and dried under vacuum at 55° C. to give the required starting material as a solid (0.286 g); NMR Spectrum: (CDCl3) 2.4 (s, 3H), 2.98 (s, 6H), 3.98 (s, 3H), 6.54 (m, 1H), 6.92 (d, 1H), 7.2 (m, 3H), 7.35 (d, 1H), 7.71 (d, 1H), 7.92 (s, 1H), 7.98 (d, 2H), 8.18 (d, 2H), 8.35 (s, 1H).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and with a saturated aqueous sodium chloride solution
  2. dry with materialThe organic solution was dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was triturated under isohexane
  5. customThe resultant solid was isolated
  6. customdried under vacuum at 55° C.
  7. customto give the

Sources & evidence

ORD record
ord-eef9276e25ff4347b4f4b0e59d87be49
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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