Sodium Iodide → 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide

HRID 848727Notes

Reaction equation

HRID 848727 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:4].[NH2:18][C:19]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21]([NH2:23])=[O:22].[I-].[Na+].[O-2].[Mg+2]>CN(C)C=O>[C:21]([C:20]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:19]=1[NH:18][CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:4])(=[O:22])[NH2:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 266222-Chloro-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-acetamideHCID 6850729Magnesium monoxideHCID 123748372-Amino-4-chlorobenzamide

Product 1

HCID 100918812-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamideYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7.73 g of 2-chloro-N-(3,4-dimetoxyphenethyl)acetamide, 5.12 g of 2-amino-4-chlorobenzamide, 13.5 g of sodium iodide and 3.63 g of magnesium oxide was added 30 ml of dimethylformamide and the resulting mixture was stirred at 90° to 100° C. for 4.5 hours. The reaction solution was concentrated under reduced pressure and the residue was extracted with 500 ml of chloroform. The chloroform extract was washed successively with 10% hydrochloric acid, water, a 5% aqueous sodium carbonate solution, a 5% aqueous sodium sulfite solution and water, dried and then concentrated to dryness under reduced pressure. The residue was recrystallized from methanol to obtain 8.01 g of 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide having a melting point of 167.5°-168.5° C.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with 500 ml of chloroform
  3. extractionThe chloroform extract
  4. washwas washed successively with 10% hydrochloric acid, water
  5. dry with materiala 5% aqueous sodium carbonate solution, a 5% aqueous sodium sulfite solution and water, dried
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-1b4f0eca18164eb1a151fd9e5085d218
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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