HCID 22129651, compound → HCID 178503308, compound

HRID 1857362Notes

Reaction equation

HRID 1857362 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[C:7]([Br:14])=[N:8][CH:9]=[C:10]([S:12][CH3:13])[N:11]=1>O.C(O)(=O)C>[Br:14][C:7]1[C:6]([OH:2])=[N:11][C:10]([S:12][CH3:13])=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 22129651HCID 22129651, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178503308HCID 178503308, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A SOLUTION OF SODIUM NITRITE (842 MG, 12.2 MMOL) IN WATER (100 ML) WAS ADDED TO A STIRRED SOLUTION OF 3-AMINO-2-BROMO-5-METHYLTHIOPYRAZINE (2.44 G, 11.1 MMOL) IN ACETIC ACID (100 ML) AT 0°C. THE REACTION WAS WARMED TO RT AND AFTER 16 H THE REACTION MIXTURE WAS PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (40% ETHYL ACETATE/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Workup

  1. customAFTER 16 H THE REACTION MIXTURE WAS PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE
  2. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  3. customEVAPORATED IN VACUO
  4. customTHE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (40% ETHYL ACETATE/HEXANES)

Sources & evidence

ORD record
ord-647481653fba4845b06134a4f577982e
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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