Acetyl chloride → 3-Thiophenecarboximidic acid ethyl ester hydrochloride

HRID 1846402Notes

Reaction equation

HRID 1846402 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]#[N:7])=[CH:2]1.[C:8]([Cl:11])(=[O:10])[CH3:9]>ClCCl.C(O)C>[ClH:11].[CH2:8]([O:10][C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[NH:7])[CH3:9]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 74231Thiophene-3-carbonitrile

Product 1

HCID 122310463-Thiophenecarboximidic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of thiophene-3-carbonitrile (10 g, 9.2 mmol) in dichloromethane (100 mL) and ethanol (170 mL) at 0° C. was added acetyl chloride (114 g, 145 mmol). The reaction was allowed to slowly warm to ambient temperature and stir 16 h. The reaction mixture was then concentrated under reduced pressure to yield a solid which was triturated with diethyl ether resulting in 17.1 g of 3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto yield a solid which
  3. customwas triturated with diethyl ether resulting in 17.1 g of 3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid

Sources & evidence

ORD record
ord-03b39457916d468483cf73e01c9afa5d
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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