Hydrochloric Acid → N-[1-(2-thienyl)-2-phenylethyl]-2-chloroacetamide

HRID 1031147Notes

Reaction equation

HRID 1031147 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl>C(Cl)(Cl)Cl>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([NH:19][C:3](=[O:4])[CH2:2][Cl:1])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 127516472-Phenyl-1-(thiophen-2-yl)ethan-1-amine

Product 1

HCID 19819816N-[1-(2-thienyl)-2-phenylethyl]-2-chloroacetamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of chloroacetyl chloride (4 mL, 0.05 mol) in chloroform (40 mL) was added dropwise to a solution of α-(2-thienyl)benzeneethanamine (10 g, 0.049 mol) and triethylamine (14 mL, 0.098 mol) in chloroform (180 mL) at 0° C. The mixture was stirred to room temperature for 1 hour. Dilute HCl (300 mL of 0.75N) was added and the reaction mixture was partitioned. The chloroform layer was separated, dried (MgSO4) and concentrated to give the amide as a light brown solid (11 g).

Workup

  1. customthe reaction mixture was partitioned
  2. customThe chloroform layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ed6ceae9fe65421094ce94c9c059af6d
Source dataset
uspto-grants-1992_04
Patent number
US05109017

Reaction notes

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