Ammonium Chloride → HCID 86689233, compound

HRID 871021Notes

Reaction equation

HRID 871021 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[C:3]=1[C:16]([NH2:18])=[O:17].[NH4+].[Cl-]>CO.[Zn]>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)[C:3]=1[C:16]([NH2:18])=[O:17]

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 86689231HCID 86689231, compound

Product 1

HCID 86689233HCID 86689233, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-(3-nitrophenyl)isothiazole-4-carboxamide (150 mg, 0.57 mmol), 0.5 mL saturated aqueous NH4Cl, and catalytic Zn powder in 6 mL MeOH was rapidly stirred at rt. After 1.5 hours additional saturated aqueous NH4Cl and catalytic Zn powder was added several times to push the reaction to completion. At 20 hours the reaction was heated at 55° C. for 6 hours, then stirred overnight at rt. The reaction was filtered using Celite and the solids rinsed with MeOH, the filtrate evaporated and treated to an aqueous workup using EtOAc and aqueous Na2CO3 to give a pale yellow solid. The solid was triturated with EtOAc/hexane to give 94 mg of faint yellow solid. Then the filtrate lot and the 94 mg of solid were separately chromatographed eluting with hexane/acetone and combined to give the title compound as an off-white solid (96 mg, 72%).

Workup

  1. customthe reaction to completion
  2. temperatureAt 20 hours the reaction was heated at 55° C. for 6 hours
  3. stirringstirred overnight at rt
  4. filtrationThe reaction was filtered
  5. washthe solids rinsed with MeOH
  6. customthe filtrate evaporated
  7. additiontreated to an aqueous workup
  8. customto give a pale yellow solid
  9. customThe solid was triturated with EtOAc/hexane

Sources & evidence

ORD record
ord-1f4fe06b07f44e558b63a77205d28ea4
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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