Allylamine → N-allyl-5-chlorothiophenecarboxamide

HRID 731573Notes

Reaction equation

HRID 731573 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.C1COCC1>[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

5

Reactant 2

HCID 7853AllylamineHCID 5892235-Chlorothiophene-2-carbonyl Chloride

Product 1

HCID 21919842N-allyl-5-chlorothiophenecarboxamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

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 THF 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-d37a5872ddbf403dad9d7df919794b7b
Source dataset
uspto-grants-2009_09
Patent number
US07585860B2

Reaction notes

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