Dichloromethane → N-(3-imidazol-1-ylpropyl)furan-2-carboxamide

HRID 1154328Notes

Reaction equation

HRID 1154328 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH2:9][CH2:10][NH2:11])[CH:7]=[CH:6][N:5]=[CH:4]1.[OH-:12].[Na+].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1Cl.Cl[CH2:21]Cl>>[N:3]1([CH2:8][CH2:9][CH2:10][NH:11][C:21]([C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 1378562-ChlorofuranHCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 3246788N-(3-imidazol-1-ylpropyl)furan-2-carboxamide

Procedure

A mixture of 1.98 g. of 1H-imidazole-1-propanamine dihydrochloride and 30 ml. of 1N sodium hydroxide was stirred at room temperature. A mixture of 0.98 ml. of 2-furanyl chloride and 50 ml. of dichloromethane was added and stirring was continued overnight. More dichloromethane was added, the organic layer was separated, washed twice with water and concentrated, giving 1.0 g. of the desired product, m.p. 111°-113° C.

Workup

  1. additionA mixture of 1.98 g
  2. additionA mixture of 0.98 ml
  3. customthe organic layer was separated
  4. washwashed twice with water
  5. concentrationconcentrated
  6. customgiving 1.0 g

Sources & evidence

ORD record
ord-c982b96588c946ce8f435a346fa595fd
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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