3-Aminobenzamide → 3-[[2-[2-(3,4-Dimethoxyphenyl)ethylamino]-2-oxoethyl]amino]benzamide

HRID 848731Notes

Reaction equation

HRID 848731 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:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH2:24])=[O:23].[I-].[Na+].C(=O)([O-])[O-].[Ca+2]>CN(C)C=O>[C:22]([C:21]1[CH:20]=[C:19]([NH:18][CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=[O:4])[CH:27]=[CH:26][CH:25]=1)(=[O:23])[NH2:24]

Participants

6

Reactant 4

HCID 16453-AminobenzamideHCID 5238Sodium IodideHCID 10112Calcium CarbonateHCID 266222-Chloro-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-acetamide

Product 1

HCID 1566513-[[2-[2-(3,4-Dimethoxyphenyl)ethylamino]-2-oxoethyl]amino]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

100 ml of dimethylformamide was added to a mixture of 25.8 g of 2-chloro-N-(3,4-dimetoxyphenethyl)acetamide, 13.6 g of m-aminobenzamide, 15.0 g of sodium iodide and 20.0 g of calcium carbonate, and the mixture was stirred at 60° C. for 4 hours. The same procedure as described in Example 1 was followed to obtain 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide. The product was converted to the corresponding hydrochloride salt as described in Example 5. The salt was recrystallized from a mixture of methanol and diethyl ether to obtain 21.7 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride having a melting point of 142°-155° C. (dec.).

Sources & evidence

ORD record
ord-d127022fb13e40e8b21bad5422700896
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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