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

HRID 2215855Notes

Reaction equation

HRID 2215855 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[C:11]#[N:12].C[OH:21]>C(OCC)(=O)C>[ClH:19].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[C:11]([NH2:12])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10858772[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into 700 ml of ethyl acetate at 0–10° C. 109.8 g (3 mol) of hydrogen chloride gas is introduced and to the solution 83 g (0.3 mol) of the [2-(2-thienyl)ethylamino](2-chorophenyl)acetonitrile of formula (I), prepared according to Example 1. or 2., and 15 ml (0.37 mol) of methanol are added and the mixture is slowly, in a period of 20 minutes, heated to 45–50° C. The reaction mixture is then stirred at 45–50° C. for 4 hours, the crystalline product is filtered off at room temperature, washed with ethyl acetate and dried. Weight: 90.4 g (91%) op.: 231–232° C. The quality of the product is identical to that of the product of Example 5.

Workup

  1. customat 0–10° C
  2. customprepared
  3. temperatureheated to 45–50° C
  4. filtrationthe crystalline product is filtered off at room temperature
  5. washwashed with ethyl acetate
  6. customdried
  7. custom231–232° C

Sources & evidence

ORD record
ord-b59ade23d6574adfa3d7b16a761778e5
Source dataset
uspto-grants-2006_09
Patent number
US07109356B2

Reaction notes

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