Allylamine → N-allyl-5-chlorothiophenecarboxamide

HRID 734285Notes

Reaction equation

HRID 734285 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[Cl:5][C:6]1[S:10][C:9]([C:11](Cl)=[O:12])=[CH:8][CH:7]=1>N1C=CC=CC=1>[CH2:1]([NH:4][C:11]([C:9]1[S:10][C:6]([Cl:5])=[CH:7][CH:8]=1)=[O:12])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 5892235-Chlorothiophene-2-carbonyl Chloride

Product 1

HCID 21919842N-allyl-5-chlorothiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An ice-cooled solution of 2.63 ml (35 mmol) of allylamine in 14.2 ml of absolute pyridine and 14.2 ml of absolute TUE is admixed dropwise with 5-chloro-thiophene-2-carbonyl chloride (7.61 g, 42 mmol). Ice-cooling is removed and the mixture is stirred at room temperature for 3 h and then concentrated under reduced pressure. The residue is admixed with water and the solid is filtered off. The crude product is purified by flash chromatography over silica gel (dichloromethane).

Workup

  1. temperatureIce-cooling
  2. customis removed
  3. concentrationconcentrated under reduced pressure
  4. filtrationthe solid is filtered off
  5. customThe crude product is purified by flash chromatography over silica gel (dichloromethane)

Sources & evidence

ORD record
ord-9ff5a6efb2474b2cb947e2950b23c2e0
Source dataset
uspto-grants-2009_09
Patent number
US07592339B2

Reaction notes

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