Bromoform → Methyl 2-bromothiazole-5-carboxylate

HRID 1414595Notes

Reaction equation

HRID 1414595 reaction equation
[N+]([O-])(OCCCCC)=O.[CH:10]([Br:13])(Br)Br.NC1[S:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=1>>[Br:13][C:10]1[S:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=1

Participants

4

Reactant 3

HCID 5558BromoformHCID 61250Amyl NitrateHCID 238005Methyl 2-aminothiazole-5-carboxylate

Product 1

HCID 2773502Methyl 2-bromothiazole-5-carboxylate

Conditions

Temperature
97.5 °C

Procedure

A mixture containing 100 g. of amyl nitrate and 600 ml. of bromoform is warmed to 70° C and then a total of 100 g. of 2- amino-5-methoxycarbonylthiazole is added portionwise with rapid stirring while maintaining the temperature at about 95-100° C. The mixture is then stirred for an additional 10 minutes at this temperature and then the bromoform is distilled off under vacuum. The residue is chromatographed on silica gel yielding 2-bromo-5-methoxycarbonylthiazole.

Workup

  1. additionA mixture containing 100 g
  2. stirringThe mixture is then stirred for an additional 10 minutes at this temperature
  3. distillationthe bromoform is distilled off under vacuum
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-1fa312e6aebd4fdea0bd755c1b275e18
Source dataset
uspto-grants-1977_01
Patent number
US04001421

Reaction notes

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