Hydrogen Peroxide → 3-(4-Methoxyphenyl)-4-methylisothiazol-5-amine

HRID 2422702Notes

Reaction equation

HRID 2422702 reaction equation
OO.[NH2:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[C:5]([CH3:9])[C:6]([NH2:8])=[S:7]>CO>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:4]2[C:5]([CH3:9])=[C:6]([NH2:8])[S:7][N:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 73012606HCID 73012606, compound

Product 1

HCID 534010803-(4-Methoxyphenyl)-4-methylisothiazol-5-amineYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add hydrogen peroxide (30% by weight, 2.39 g, 70.3 mmol) to a solution of 3-amino-3-(4-methoxyphenyl)-2-methyl-thioacrylamide (7.800 g, 35.135 mmol) in methanol (703 mL). Stir 3 h. Quench the reaction with Na2S2O3 (20% in water) and evaporate to 10 mL. Dilute with EtOAc (500 mL) and wash the organic phase with brine (3×100 mL), evaporate and crystallize from EtOAc/hexane to afford 3-(4-methoxy-phenyl)-4-methylisothiazol-5-ylamine. Yield: 88.2%. ES-MS: m/e 221.0 (m+1).

Workup

  1. customQuench
  2. customthe reaction with Na2S2O3 (20% in water)
  3. customevaporate to 10 mL
  4. additionDilute with EtOAc (500 mL)
  5. washwash the organic phase with brine (3×100 mL)
  6. customevaporate
  7. customcrystallize from EtOAc/hexane

Sources & evidence

ORD record
ord-0bc87021aae74ea1bc1d4c5772df4842
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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