4-(4-Nitrophenyl)thiomorpholine 1,1-dioxide → 4-(4-Aminophenyl)thiomorpholine 1,1-Dioxide

HRID 1910821Notes

Reaction equation

HRID 1910821 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Zn]>[O:17]=[S:13]1(=[O:16])[CH2:12][CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 114595184-(4-Nitrophenyl)thiomorpholine 1,1-dioxide

Product 1

HCID 263703844-(4-Aminophenyl)thiomorpholine 1,1-DioxideYield 51.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Zinc powder (0.47 g, 7.2 mmol) was added to a solution of 4-(4-nitro-phenyl)-thiomorpholine 1,1-dioxide (155 mg, 0.60 mmol) in acetic acid (3 mL) and the mixture was stirred at 60° C. for 2 h. The reaction mixture was concentrated to dryness, diluted with ethyl acetate and washed with sodium bicarbonate solution and water then dried over sodium sulfate. The organic layer was concentrated to dryness to afford 4-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-phenylamine (70 mg, 51%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with ethyl acetate
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialthen dried over sodium sulfate
  5. concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-175e5fda9a604c0e9908885033786874
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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