2,3-Difluoro-6-nitroaniline → HCID 23439407, compound

HRID 2120375Notes

Reaction equation

HRID 2120375 reaction equation
[CH3:1][CH:2]([S-:4])[CH3:3].[Na+].[F:6][C:7]1[C:13](F)=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:8]=1[NH2:9]>CN(C=O)C.CCOC(C)=O>[F:6][C:7]1[C:13]([S:4][CH:2]([CH3:3])[CH3:1])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 27370282,3-Difluoro-6-nitroanilineHCID 3470666Sodium 2-propanethiolate

Product 1

HCID 23439407HCID 23439407, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium 2-propanethiolate (5.66 g) was added to a solution of 2,3-difluoro-6-nitroaniline (10.04 g) in DMF (200 ml). The mixture was stirred at ambient temperature for 16 hours and then diluted with EtOAc (300 ml) and washed with brine (500 ml). The washing was extracted with EtOAc (300 ml). The organic phases were combined, washed with brine (500 ml), dried and volatile material was removed by evaporation to give the title compound (14.1 g) as a solid. NMR: 1.30 (d, 6H), 3.70 (septet, 1H), 6.70 (dd, 1H), 7.26 (s, 2H), 7.80 (dd, 1H); m/z 229.

Workup

  1. washwashed with brine (500 ml)
  2. extractionThe washing was extracted with EtOAc (300 ml)
  3. washwashed with brine (500 ml)
  4. customdried
  5. customvolatile material was removed by evaporation

Sources & evidence

ORD record
ord-2b1df194d5e24df8b4bd4728619fe43b
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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