Sodium Dithionite → HCID 68603610, compound

HRID 448896Notes

Reaction equation

HRID 448896 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-1bc37219eea542bf853320eb001bb0ba
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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