Dimethylformamide → HCID 22009755, compound

HRID 322360Notes

Reaction equation

HRID 322360 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:19]=[C:20](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:21][CH:22]=2)=[CH:12][CH:11]=1)(=O)=O.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[C:36]([O:38][CH2:39][CH3:40])=[O:37].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:25]1(/[CH:24]=[CH:23]/[C:20]2[O:21][CH:22]=[C:18]([CH2:17][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:31]4[CH:35]=[CH:34][N:33]=[C:32]4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][CH:14]=3)[N:19]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 549404ethyl 1H-imidazole-2-carboxylateHCID 15521676HCID 15521676, compound

Product 1

HCID 22009755HCID 22009755, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butyl methanesulfonate (430 mg), ethyl 2-imidazolecarboxylate (155 mg), potassium carbonate (305 mg) and N,N-dimethylformamide (10 ml) was stirred for two hours at temperatures ranging from 80 to 90° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to a silica gel column chromatography. The crystalline product obtained from the fraction eluted with ethyl acetate-hexane (2:1, v/v) was recrystallized from ethyl acetate-hexane to give ethyl 1-[4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butyl]-2-imidazolecarboxylate (280 mg, 60%) as colorless prisms, mp 96-97° C.

Workup

  1. customranging from 80 to 90° C
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crystalline product obtained from the fraction
  7. washeluted with ethyl acetate-hexane (2:1
  8. customv/v) was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2d0ad6fe44d046ecb27a0629db21091f
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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