Sodium Chloride → HCID 15077510, compound

HRID 1074210Notes

Reaction equation

HRID 1074210 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=1.F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].[Cl-].[Na+]>CN(C)C=O.O.C(O)(=O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([S:3][C:4]2[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 677672,5-DifluoronitrobenzeneHCID 178480602HCID 178480602, compound

Product 1

HCID 15077510HCID 15077510, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.6 g of 60% sodium hydride in mineral oil in 25 ml of N,N-dimethylformamide was added 1.1 g (10 mmoles) of 2-mercapto-1-methylimidazole. After stirring for 30 minutes, 1.6 g (10 mmoles) of 2,5-difluoronitrobenzene was added and the mixture stirred at room temperature for 16 hours. After adding 0.5 ml of acetic acid, the mixture was poured into a mixture of ice, water and sodium chloride. After standing for 1 hour the solid was collected by filtration, washed with water and dried. The crude product was purified by chromatography on silica gel using ethyl acetate as the eluent. The fractions containing the product were combined and concentrated to give 0.7 g (28%) of the product as yellow prisms, mp 123°-126° C.

Workup

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. waitAfter standing for 1 hour
  3. filtrationthe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe crude product was purified by chromatography on silica gel
  7. additionThe fractions containing the product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9ac19751ef3245d0913c5c89db1ee899
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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