Hydrochloric Acid → [2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride

HRID 323885Notes

Reaction equation

HRID 323885 reaction equation
C(OC)(=[O:3])C.Cl.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][NH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[C:16]#[N:17].CO>>[ClH:24].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][NH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[C:16]([NH2:17])=[O:3]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 6584Methyl AcetateHCID 10858772[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

Product 1

HCID 21953219[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride

Conditions

Temperature
22.5 °C

Procedure

Into 1200 ml of methyl acetate 204 g (5.6 mol) of hydrogen chloride gas is introduced at 15-25° C., and to the solution 221.4 g (0.8 mol) of the [2-(2-thienyl)ethylamino](2-chlorophenyl)acetonitrile of formula (I), prepared as described in Example 1., and 48 ml (1.2 mol) of methanol are added and the mixture is stirred at 20-25° C. for 6 hours. In the course of the reaction first the hydrochloride of the starting “nitrile”, then gradually the hydrochloride of the resulting “acid amide” precipitates, in the form of white crystals. The crystals are collected by filtration, washed with methyl acetate and dried. Weight: 249 g (94%) mp.: 231-232° C.

Workup

  1. customgradually the hydrochloride of the resulting “acid amide” precipitates, in the form of white crystals
  2. filtrationThe crystals are collected by filtration
  3. washwashed with methyl acetate
  4. customdried

Sources & evidence

ORD record
ord-f4a7dd8fee7148799c35afe14e004dcf
Source dataset
uspto-grants-2001_04
Patent number
US06215005B1

Reaction notes

Loading…