Sodium Dithionite → HCID 68603610, compound

HRID 661649Notes

Reaction equation

HRID 661649 reaction equation
[Cl:1][C:2]1[C:18]([N+:19]([O-])=O)=[CH:17][C:5]([C:6]([N:8]([CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:7])=[C:4]([F:22])[CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>O.C1COCC1>[NH2:19][C:18]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([CH:17]=1)[C:6]([N:8]([CH3:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:7]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 68603780HCID 68603780, compound

Product 1

HCID 68603610HCID 68603610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-chloro-2-fluoro-N-methyl-5-nitro-N-o-tolyl-benzamide (6.6 g, 20.3 mmol) was stirred vigorously in a mixture of water (30 mL) and THF (30 mL) containing Na2S2O4 (17.6 g, 101.2 mmol) for 12 hrs. The organic layer was then separated and the water layer was further extracted with ethyl acetate. The combined organic solutions were washed with brine and dried over MgSO4. Concentration yielded 5-amino-4-chloro-2-fluoro-N-methyl-N-o-tolyl-benzamide as a crude solid which was washed with ether to give a light yellow product (3.3 g). MS: 292.9 (M+H)+: tR=1.90 min (method 1)

Workup

  1. customThe organic layer was then separated
  2. extractionthe water layer was further extracted with ethyl acetate
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-dca568060d40476fa94ece137e3a662d
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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