Dimethylamine → HCID 15615542, compound

HRID 1194319Notes

Reaction equation

HRID 1194319 reaction equation
[C:1]([C:4]1[O:8][C:7]([C:9](Cl)=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:12][NH:13][CH3:14]>O1CCCC1>[CH3:12][N:13]([CH3:14])[C:9]([C:7]1[O:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:10]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 156155415-Acetylfuran-2-carbonyl chloride

Product 1

HCID 15615542HCID 15615542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 9.1 g. (0.053 mole) of 5-acetylfuran-2-carbonyl chloride in 150 ml. of tetrahydrofuran at ca -30° C. was added, dropwise, 7.0 ml. (0.106 mole) of dimethylamine. Stirring was continued, and the reaction mixture was allowed to warm to room temperature and then stirred overnight. The tetrahydrofuran was removed by evaporation in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The extracts were washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with 1:20 methanol-chloroform, to give 7.33 g. of the title compound as a solid, mp 101°-104° C. A small sample was recrystallized from cyclohexane to give a pale yellow solid, mp. 104°-106° C.

Workup

  1. stirringstirred overnight
  2. customThe tetrahydrofuran was removed by evaporation in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with 1:20 methanol-chloroform
  10. customto give 7.33 g

Sources & evidence

ORD record
ord-79d3b29750484b60b21e5f529f31bad2
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

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