Trimethylsilyldiazomethane → 6-Methoxy-2-methyl-1,3-benzothiazole-7-carbaldehyde

HRID 1290008Notes

Reaction equation

HRID 1290008 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[C:3]=1[CH:12]=[O:13].[CH3:14][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[CH3:14][O:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[C:3]=1[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 189223346-Hydroxy-2-methyl-1,3-benzothiazole-7-carbaldehyde

Product 1

HCID 189223726-Methoxy-2-methyl-1,3-benzothiazole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

6-Hydroxy-2-methyl-benzothiazole-7-carboxaldehyde (75 mg, 0.362 mmol) was taken up in 30% methanol in benzene (7 mL) and treated with (trimethylsilyl)diazomethane (2.0M solution in hexanes) (0.5 mL, 1.0 mmol) for 2 hours at room temperature. The mixture was evaporated, and the title compound was purified by flash chromatography eluting with 25-30% ethyl acetate in hexane.

Workup

  1. customThe mixture was evaporated
  2. customthe title compound was purified by flash chromatography
  3. washeluting with 25-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f8f14fed026942cb864cb3031c4b8dd8
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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