Dimethylformamide → Methyl [4-methyl-2-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylthio]thiazol-5-yl]acetate

HRID 1295332Notes

Reaction equation

HRID 1295332 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:7])[N:6]=1.Cl[CH2:14][C:15]1[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=1)[O:18][CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:7][C:5]1[N:6]=[C:2]([S:1][CH2:14][C:15]2[CH:34]=[CH:33][CH:32]=[C:17]([O:18][CH2:19][C:20]3[N:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:23][C:24]=3[CH3:25])[CH:16]=2)[S:3][C:4]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 178499653HCID 178499653, compound

Product 1

HCID 86591689Methyl [4-methyl-2-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylthio]thiazol-5-yl]acetateYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl (2-mercapto-4-methylthiazol-5-yl)acetate (385 mg), 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (600 mg), potassium carbonate (400 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 methyl [4-methyl-2-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylthio]thiazol-5-yl]acetate (665 mg, yield 72%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:3 volume ratio).

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-d7da7e989fdb4686918fbfacd01d672f
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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