Dimethylformamide → HCID 178471186, compound

HRID 1295292Notes

Reaction equation

HRID 1295292 reaction equation
[SH:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:3]=1.Cl[CH2:15][C:16]1[CH:35]=[CH:34][C:19]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:27][C:26]1[O:25][C:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:23][C:22]=1[CH2:21][O:20][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][S:1][C:2]2[NH:6][N:5]=[C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:3]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 178471187HCID 178471187, compound

Product 1

HCID 178471186HCID 178471186, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(5-mercapto-1H-1,2,4-triazol-3-yl)propionate (450 mg), 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (700 mg), potassium carbonate (370 mg) and N,N-dimethylformamide (20 ml) was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylthio]-1H-1,2,4-triazol-3-yl]propionate was obtained as crystals (600 mg, yield 56%) from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 114–115° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-579bd58ff8614bbcb6fc71e270e29a4e
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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