Hydrochloric Acid → Ici 222155

HRID 1195130Notes

Reaction equation

HRID 1195130 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([CH2:15][N+:16]([O-:18])=[O:17])(=[O:14])=[O:13])=[C:7]([CH3:19])[CH:6]=1)(=O)C.Cl.O>C(O)C>[NH2:4][C:5]1[CH:6]=[C:7]([CH3:19])[C:8]([S:12]([CH2:15][N+:16]([O-:18])=[O:17])(=[O:14])=[O:13])=[C:9]([CH3:11])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 15447075(4-Acetamido-2,6-dimethylphenylsulfonyl)nitromethane

Product 1

HCID 195716Ici 222155Yield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Acetamido-2,6-dimethylphenylsulfonyl)nitromethane (11.5 g, 40 mM) is added in one portion to a boiling mixture of concentrated hydrochloric acid (22 mL), water (110 mL) and ethanol (45 mL). The mixture is stirred at reflux until a clear solution formed (about 20 minutes) and then for a further 10 mins. The hot reaction mixture is then poured into an excess of ice-cold saturated sodium bicarbonate solution. The aqueous mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (MgSO4) and the solvent removed by evaporation to give (4-amino-2,6-dimethylphenylsulfonyl)nitromethane, as a solid, m.p. 132°-133° C. [after recrystallisation from ethanol] in 73% yield; NMR(d6 -DMSO, 200 MHz): 2.39(6H, s), 6.19(4H, s), 6.35(2H, s); microanalysis, found: C,44.5; H,4.9; N,11.6%; C9H12N2O4S requires: C,44.3; H,4.9; N,11.5%.

Workup

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

Sources & evidence

ORD record
ord-8fd03b0fcc0a41a58de7e533de2f3a14
Source dataset
uspto-grants-1992_05
Patent number
US05110808

Reaction notes

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