Ammonium Chloride → N-(5-amino-4-chloro-2-methylphenyl)methanesulfonamide

HRID 889447Notes

Reaction equation

HRID 889447 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:4]([CH3:16])[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Zn]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([CH3:16])=[C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67359857N-(4-chloro-2-methyl-5-nitrophenyl)methanesulfonamide

Product 1

HCID 67357473N-(5-amino-4-chloro-2-methylphenyl)methanesulfonamideYield 96.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of Intermediate 79A (175 mg, 0.66 mmol), zinc (432 mg, 6.61 mmol), ammonium chloride (354 mg, 6.61 mmol) in ethanol (10 mL) and water (5.0 mL) was heated to reflux for 30 min. The reaction mixture was concentrated, suspended in ethyl acetate and filtered. The filtrate was washed with water, aqueous NaHCO3 and brine, dried over MgSO4 and concentrated to give Intermediate 79 (149 mg, 96%) as a white solid. HPLC: Rt=0.453 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). MS (ES): m/z=235 [M+H]+. Intermediate 79 was used in the synthesis of Example 243.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. filtrationfiltered
  5. washThe filtrate was washed with water, aqueous NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fce048a090fd4352840d139c20efe8fb
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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