Allylamine → N-allyl-5-chlorothiophenecarboxamide

HRID 68470

Reaction equation

HRID 68470 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-c02ce5a6e4d64658935876d0d60677c1
Source dataset
uspto-grants-2014_09
Patent number
US08822458B2

Linked notes

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