Allylamine → N-allyl-5-chlorothiophenecarboxamide

HRID 499735Notes

Reaction equation

HRID 499735 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[CH2:10]([NH2:13])[CH:11]=[CH2:12]>N1C=CC=CC=1.C1COCC1>[CH2:10]([NH:13][C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:8])[CH:11]=[CH2:12]

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

5-Chlorothiophene-2-carbonyl chloride (7.61 g, 42 mmol) is added dropwise to 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. The ice cooling is removed and the mixture is stirred at room temperature for 3 h before being concentrated in vacuo. Water is added to the residue, and the solid is filtered off. The crude product is purified by flash chromatography on silica gel (dichloromethane).

Workup

  1. customThe ice cooling is removed
  2. concentrationbefore being concentrated in vacuo
  3. additionWater is added to the residue
  4. filtrationthe solid is filtered off
  5. customThe crude product is purified by flash chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-0b2bbe232f0449b682a3aff724facdad
Source dataset
uspto-grants-2010_08
Patent number
US07767702B2

Reaction notes

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