2-Bromo-5-nitrothiazole → HCID 178434161, compound

HRID 1422032Notes

Reaction equation

HRID 1422032 reaction equation
Br[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.[SH:10][C:11]1[S:12][C:13]([CH3:16])=[N:14][N:15]=1>C(O)C.[OH-].[K+]>[N+:7]([C:4]1[S:3][C:2]([S:10][C:11]2[S:12][C:13]([CH3:16])=[N:14][N:15]=2)=[N:6][CH:5]=1)([O-:9])=[O:8].[SH:10][C:11]1[S:12][C:13]([CH3:16])=[N:14][N:15]=1

Participants

6

Reactant 2

HCID 182112-Bromo-5-nitrothiazoleHCID 178434161HCID 178434161, compound

Product 2

HCID 15551238HCID 15551238, compoundHCID 178434161HCID 178434161, compoundYield 151.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

Alternatively, 2-[(5-nitrothiazol-2-yl)mercapto]-5-methyl-1,3,4-thiadiazole is prepared by the general method of J Bourdais, P Dauvillier, P Gayral, M-C Rigothie, P Timon-David et al, 1981. Eur. J. Chem. Chim. Ther. 16: 233-240. 2-Bromo-5-nitrothiazole (2.09 g) and 1.32 g of 2-mercapto-5-methyl-1,3,4-thiadiazole in 10 mL of ethanol and 10 mL of 1 N potassium hydroxide are stirred at room temperature overnight. The precipitated solid is collected by vacuum filtration, washed with water and crystallized from ethyl acetate/hexane to give 1 g of the title compound as an off-white solid.

Workup

  1. filtrationThe precipitated solid is collected by vacuum filtration
  2. washwashed with water
  3. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c66a6f35363498185c4fad3c3e380b3
Source dataset
uspto-grants-2000_06
Patent number
US06080772

Reaction notes

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