N-bromobutanimide → HCID 22129651, compound

HRID 1857361Notes

Reaction equation

HRID 1857361 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[N:15]=[C:14]([S:16][CH3:17])[CH:13]=[N:12][CH:11]=1>C(Cl)(Cl)Cl>[NH2:9][C:10]1[C:11]([Br:8])=[N:12][CH:13]=[C:14]([S:16][CH3:17])[N:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 221296536-(Methylsulfanyl)pyrazin-2-amine

Product 1

HCID 22129651HCID 22129651, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

NBS (3.28 G, 18.4 MMOL) WAS SLOWLY ADDED TO A STIRRED SOLUTION OF 6-AMINO-2-METHYLTHIOPYRAZINE (2.6 G, 18.4 MMOL) IN CHLOROFORM (100 ML). AFTER 1 H THE REACTION MIXTURE WAS PARTITIONED BETWEEN 10% SODIUM METABISULFITE SOLUTION AND CHLOROFORM. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (20% ETHYL ACETATE/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID: 1H NMR (CDCL3): Δ 2.49 (S, 3H), 4.97 (BR S, 2H), 7.59 (S, 1H).

Workup

  1. customAFTER 1 H THE REACTION MIXTURE WAS PARTITIONED BETWEEN 10% SODIUM METABISULFITE SOLUTION AND CHLOROFORM
  2. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  3. customEVAPORATED IN VACUO
  4. customTHE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (20% ETHYL ACETATE/HEXANES)

Sources & evidence

ORD record
ord-f2f83daa52f84ad5a875c75d3799d798
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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