Hydrochloric Acid → HCID 10680224, compound

HRID 465498Notes

Reaction equation

HRID 465498 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][N+:15]([O-:17])=[O:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.Cl.O>C(O)C>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][N+:15]([O-:17])=[O:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 2744911HCID 2744911, compound

Product 1

HCID 10680224HCID 10680224, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Acetamidophenylsulphonyl)nitromethane (obtained as described in J Het. Chem., 1977, 14, 1415) (10.0 g, 38.8 mmol) was added in one portion to a boiling mixture of concentrated hydrochloric acid (20 ml), water (100 ml) and ethanol (40 ml). The mixture was stirred at reflux until a clear solution formed (about 20 minutes) and then for a further 5 mins. The hot reaction mixture was poured into an excess of ice-cold saturated sodium bicarbonate solution and then extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and the solvent was removed by evaporation. There was thus obtained (4 aminophenylsulphonyl)nitromethane as a pale yellow solid (5.2 g, 62% yield), m.p. 132°-133° C., microanalysis, found: C, 39.2; H, 3.8: N, 12.9%; C7H8N2O4S requires: C, 38.9; H, 3.7; N, 12.95%.

Workup

  1. temperatureat reflux until a clear solution
  2. customformed (about 20 minutes)
  3. additionThe hot reaction mixture was poured into an excess of ice-cold saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b8b793c5fff2499db5c2cea31541b00f
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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