Triethylamine → N-[2-chloro-5-(3-dimethylaminobenzamido)phenyl]-3,4-dimethoxybenzamide

HRID 991417Notes

Reaction equation

HRID 991417 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:18])[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:39])=[C:24]([NH:26][C:27](=[O:38])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=2)[CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.CN(C)C1C=CN=CC=1>[Cl:39][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:9]([N:8]([CH3:7])[CH3:18])[CH:10]=2)=[CH:25][C:24]=1[NH:26][C:27](=[O:38])[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 668373-(Dimethylamino)benzoic acidHCID 18413853N-(5-amino-2-chlorophenyl)-3,4-dimethoxybenzamide

Product 1

HCID 9846740N-[2-chloro-5-(3-dimethylaminobenzamido)phenyl]-3,4-dimethoxybenzamideYield 24.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.11 ml) was added dropwise to a stirred suspension of 3-dimethylaminobenzoic acid (0.18 g) in methylene chloride (10 ml) at 20° C. DMF (2 drops) was added and the reaction mixture was stirred for 4 hours. The solvent was evaporated to give a solid. The solid was dissolved in methylene chloride (15 ml) and added dropwise over 5 minutes to a stirred mixture of N-(5-amino-2-chlorophenyl)-3,4-dimethoxybenzamide (0.306 g), triethylamine (0.4 ml), 4-dimethylaminopyridine (0.005 g) and methylene chloride (5 ml). The resultant mixture was stirred at 20° C. for 18 hours. The reaction mixture was washed with water and with a saturated, aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.109 g), m.p. 98-99° C.;

Workup

  1. customThe solvent was evaporated
  2. customto give a solid
  3. washThe reaction mixture was washed with water
  4. dry with materialwith a saturated, aqueous sodium bicarbonate solution, dried (MgSO4)
  5. customevaporated
  6. customThe residual oil was purified by column chromatography on silica gel using
  7. additiona 99:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-f85a736d67cc4f9e966acb66ba2014c6
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

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