Water → [2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide

HRID 434172Notes

Reaction equation

HRID 434172 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[C:11]([NH2:13])=[O:12].O.[OH-].[Na+]>ClCCCl>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21953219[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride

Product 1

HCID 9882604[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

24.8 g (0.075 mol) of [2-(2-thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride, prepared according to example 5. or 6., is mixed with 170 ml of water, then under mild cooling 30 ml of 10% sodium hydroxide solution and 170 ml of 1,2-dichloroethane are added. The phases are separated, the aqueous phase is extracted with 2×20 ml of 1,2-dichloroethane, the combined organic layer is evaporated in vacuo. Residue: 22 g, fast crystallizing oil. The crude product is recrystallized from 80 ml of isopropyl acetate to give 19,5 g of the crystalline base of formula (VII). Yield: 88,2%, mp.: 90-92° C.

Workup

  1. additionare added
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with 2×20 ml of 1,2-dichloroethane
  4. customthe combined organic layer is evaporated in vacuo
  5. customResidue: 22 g, fast crystallizing oil
  6. customThe crude product is recrystallized from 80 ml of isopropyl acetate

Sources & evidence

ORD record
ord-51bb191dc4094e5b913ce9afa40b9bfa
Source dataset
uspto-grants-2003_12
Patent number
US06670486B1

Reaction notes

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