Veratroyl chloride → N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamide

HRID 991429Notes

Reaction equation

HRID 991429 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[NH2:14][C:15]1[C:16]([Cl:34])=[CH:17][C:18]([F:33])=[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=2)[CH:20]=1>N1C=CC=CC=1>[Cl:34][C:16]1[CH:17]=[C:18]([F:33])[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:30])[CH3:31])[CH:24]=2)=[CH:20][C:15]=1[NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 77070Veratroyl chlorideHCID 22732310N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide

Product 1

HCID 9847600N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamideYield 27.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3,4-dimethoxybenzoyl chloride (0.5 g), N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide (0.781 g) and pyridine (8 ml) was stirred at ambient temperature for 18 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous copper sulphate solution. The organic phase was washed in turn with water and a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.328 g);

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. washThe organic phase was washed in turn with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 99:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-206ad1cdf15246a18208d54689358a07
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

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