Ammonium Chloride → HCID 71621924, compound

HRID 871017Notes

Reaction equation

HRID 871017 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[C:3]=1[C:16]([NH2:18])=[O:17].[NH4+].[Cl-]>[NH4+].[Cl-].CO.[Zn]>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)[C:3]=1[C:16]([NH2:18])=[O:17]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 71621923HCID 71621923, compound

Product 1

HCID 71621924HCID 71621924, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst3×HCID 25517Ammonium ChlorideCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-(4-nitrophenyl)isothiazole-4-carboxamide (63 mg, 0.24 mmol), 12 drops saturated aqueous NH4Cl, and catalytic Zn powder in 4 mL MeOH was rapidly stirred at rt. After 1.5 hours additional saturated aqueous NH4Cl (6 drops) and catalytic Zn powder was added and the reaction heated at 55° C. Then additional solid NH4Cl and catalytic Zn powder was added to push the reaction to completion. At 4 hours the reaction was filtered using Celite and the solids rinsed with MeOH and EtOAc, the filtrate evaporated and treated to an aqueous workup using EtOAc and saturated aqueous NaHCO3 to give a yellow gummy solid. This material was triturated with 20% EtOAc/hexane to give the title compound as a yellow-beige solid (53 mg, 94%).

Workup

  1. temperaturethe reaction heated at 55° C
  2. customthe reaction to completion
  3. filtrationAt 4 hours the reaction was filtered
  4. washthe solids rinsed with MeOH and EtOAc
  5. customthe filtrate evaporated
  6. additiontreated to an aqueous workup
  7. customto give a yellow gummy solid
  8. customThis material was triturated with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-9e513a5b901340ee820bc75dbe3d65e4
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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