Acetone → HCID 66937253, compound

HRID 538139Notes

Reaction equation

HRID 538139 reaction equation
[Cl:1][C:2]1[C:7]([S:8][C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]([NH2:16])=[C:4]([N+:17]([O-])=O)[CH:3]=1.[Cl-].[NH4+].CC(C)=O>[Zn].O>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH2:16])=[CH:6][C:7]=1[S:8][C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 66937535HCID 66937535, compound

Product 1

HCID 66937253HCID 66937253, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To an ice bath cooled solution (0° C.) of 4-chloro-2-nitro-5-m-tolylsulfanyl-phenylamine (2.30 g, 7.80 mmol), ammonium chloride (6.26 g, 117 mmol), acetone (32.5 mL), and water (6.5 mL) was added portion-wise zinc powder (5.10 g, 78.0 mmol). The reaction mixture was removed from the ice bath and after 30 min, the reaction mixture was filtered through a pad of Celite® and washed with EtOAc. The filtrate was placed in a sep funnel and the organic layer was collected. The organic layers dried, filtered, and concentrated under reduced pressure. The crude material was used without further purification in the next reaction.

Workup

  1. customThe reaction mixture was removed from the ice bath and after 30 min
  2. filtrationthe reaction mixture was filtered through a pad of Celite®
  3. washwashed with EtOAc
  4. customThe filtrate was placed in a sep funnel
  5. customthe organic layer was collected
  6. customThe organic layers dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was used without further purification in the next reaction

Sources & evidence

ORD record
ord-e8250f268ab34d44a55cb981ae95dc55
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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