Trimethylsilyldiazomethane → HCID 18922481, compound

HRID 1290002Notes

Reaction equation

HRID 1290002 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:18][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[CH3:18][O:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 135761798HCID 135761798, compound

Product 1

HCID 18922481HCID 18922481, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a mixture of ethyl 4-hydroxy-2-(4-pyridyl)-thiazole-5-carboxylate (0.5 gm, 2.0 mmol) in 30% methanol in benzene (30 mL) was added (trimethylsilyl)diazomethane (2.0M solution in hexanes) (1.0 mL, 2.0 mmol). After stirring for 30 minutes at room temperature, an additional 1.0 mL of (trimethylsilyl)diazomethane was added. The mixture was stirred overnight at room temperature and evaporated. The title compound was purified by flash chromatography eluting with 20% acetone in hexane; yield 206 mg.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customevaporated
  3. customThe title compound was purified by flash chromatography
  4. washeluting with 20% acetone in hexane

Sources & evidence

ORD record
ord-f1cfea04bc1643a6a8e664d8d3da0871
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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