Trimethylsilyldiazomethane → Methyl 2-bromobenzo[d]thiazole-6-carboxylate

HRID 447157Notes

Reaction equation

HRID 447157 reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[Br:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 457896282-Bromo-1,3-benzothiazole-6-carboxylic acid

Product 1

HCID 46911877Methyl 2-bromobenzo[d]thiazole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-6-benzothiazolecarboxylic acid (0.500 g, 1.94 mmol) was suspended in dichloromethane/methanol (12 ml, 6:1) and cooled to 0° C. with an ice-water bath. Then, 2M (trimethylsilyl)diazomethane (2.91 ml, 5.81 mmol) was added dropwise over 5 min. The resulting mixture was warmed to room temperature and stirred at room temperature for 2 hrs. The resulting mixture was concentrated in vacuo to yield methyl 2-bromobenzo[d]thiazole-6-carboxylate.

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a662a9a1502142b7b205449252c82d31
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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