Acetyl chloride → 3-Thiophenecarboximidic acid ethyl ester hydrochloride

HRID 714426Notes

Reaction equation

HRID 714426 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-4e8f02e2d17f4b3393fe004aab38174e
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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