Water → HCID 11265014, compound

HRID 1595823Notes

Reaction equation

HRID 1595823 reaction equation
[H-].[Na+].[SH:3][C:4]1[S:5][CH:6]=[CH:7][N:8]=1.[Cl:9][C:10]1[CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][C:15]=1F.O>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[S:3][C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[NH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 178527881HCID 178527881, compound

Product 1

HCID 11265014HCID 11265014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 3.8 g sodium hydride (60% in mineral oil) in 100 ml of dimethylformamide was added slowly a solution of 10.0 g of 2-mercapto thiazole in 100 ml of dimethylformamide. After 15 min a solution of 15.0 g 3-chloro-4-fluoro nitrobenzene in 50 ml of dimethylformamide was added. After 4 hrs, the mixture was poured into water. The resulting solid was collected, washed with water, and dried in vacuum. This material was mechanically stirred at reflux in a mixture of 830 ml of methanol, 230 ml of water, 37.0 g of ammonium chloride, and 30.1 g of iron powder for 4 hrs. The boiling mixture was filtered. The solvent was removed from the filtrate and the residue was extracted with hot ethyl acetate. The ethyl acetate solution was filtered through a short silica gel column. The solvent was removed and the residue was recrystallized from ether hexane giving 17.7 g of an off white solid.: mass spectrum electrospray, m/e): M+H 243.1.

Workup

  1. customThe resulting solid was collected
  2. washwashed with water
  3. customdried in vacuum
  4. temperatureat reflux in a mixture of 830 ml of methanol, 230 ml of water, 37.0 g of ammonium chloride, and 30.1 g of iron powder for 4 hrs
  5. filtrationThe boiling mixture was filtered
  6. customThe solvent was removed from the filtrate
  7. extractionthe residue was extracted with hot ethyl acetate
  8. filtrationThe ethyl acetate solution was filtered through a short silica gel column
  9. customThe solvent was removed
  10. customthe residue was recrystallized from ether hexane giving 17.7 g of an off white solid

Sources & evidence

ORD record
ord-d983c11fa9f74baabbf37797613a1797
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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