Water → HCID 15278732, compound

HRID 1459284Notes

Reaction equation

HRID 1459284 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[S:18][CH2:19][CH3:20])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>[Zn].C(O)C>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([S:18][CH2:19][CH3:20])=[C:9]([S:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:8])=[O:7])[CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 15278731HCID 15278731, compound

Product 1

HCID 15278732HCID 15278732, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

13.3 g of zinc powder are added in portions to a mixture of 12 g of N-tert-butyl-2-ethylmercapto-5-nitrobenzenesulfonamide, 17.7 g of ammonium chloride, 50 ml of water and 200 ml of ethanol and the mixture is stirred at 70° C. for 10 hours. After the solid has been filtered off and washed out with ethyl acetate, the filtrate is concentrated under reduced pressure. The residue from the filtrate is taken up in ethyl acetate and the mixture is washed with water. After drying over magnesium sulfate, the organic phase is concentrated. 9.4 g of the desired aniline are thus obtained;

Workup

  1. filtrationAfter the solid has been filtered off
  2. washwashed out with ethyl acetate
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. washthe mixture is washed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-bb8d6c6ca6e348fb896ac5870e106af7
Source dataset
uspto-grants-1998_12
Patent number
US05854179

Reaction notes

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