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

HRID 848734Notes

Reaction equation

HRID 848734 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]([NH:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[O:14])[CH:8]=[CH:9][CH:10]=1)(=[O:4])[NH2:3].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(Cl)(Cl)Cl>[C:2]([C:5]1[CH:6]=[C:7]([NH:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[O:14])[CH:8]=[CH:9][CH:10]=1)(=[O:4])[NH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 156650Benzamide, 3-((2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)amino)-, monohydrochloride

Product 1

HCID 1566513-[[2-[2-(3,4-Dimethoxyphenyl)ethylamino]-2-oxoethyl]amino]benzamideYield 84.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3.0 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride were added 20 ml of 5% aqueous sodium carbonate solution and 125 ml of chloroform and then the mixture was stirred at room temperature until the hydrochloride completely dissolved. The chloroform layer was separated, washed with water, dried and the solvent was concentrated to dryness under reduced pressure. The residue was crystallized from a mixture of methanol and diethyl ether to obtain 2.3 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide having a melting point of 133° to 135° C.

Workup

  1. dissolutioncompletely dissolved
  2. customThe chloroform layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationthe solvent was concentrated to dryness under reduced pressure
  6. customThe residue was crystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-3a31c8b44cee439a957277104d2be050
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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