Ammonium → 4-chloro-1H-pyrrole-2-carboxamide

HRID 1094874

Reaction equation

HRID 1094874 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:6][CH:7]=[C:8]([Cl:10])[CH:9]=1)=[O:4].[NH4+:13]>C1COCC1>[Cl:10][C:8]1[CH:9]=[C:5]([C:3]([NH2:13])=[O:4])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 223AmmoniumHCID 71306882,2,2-trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethan-1-one

Product 1

HCID 552075774-chloro-1H-pyrrole-2-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,2-trichloro-1-(4-chloro-1H-Pyrrol-2-yl)ethanone (14.0 g, 56.7 mmol) in THF (100 mL) was bubbled with ammonium gas for 2 h at room temperature. TLC analysis indicated that there was complete conversion of starting material. The reaction mixture was concentrated in vacuo to yield 7.5 g of the above compound (51.88 mmol, yield 92%). 1H-NMR (Acetone-d6) δ 10.92 (br s, 1H), 7.21 (br s, 1H), 7.02 (s, 1H), 6.84 (s, 1H), 6.57 (br s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ea773c68d66d43b68f03ceb3da912e31
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Linked notes

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