Hydrochloric Acid → HCID 19966720, compound

HRID 976224Notes

Reaction equation

HRID 976224 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:8][S:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH2:20])(=[O:19])=[O:18])=[O:10].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[CH2:1]([NH:5][C:6]([NH:20][S:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:9]([CH3:8])=[O:10])(=[O:19])=[O:18])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 19966719HCID 19966719, compound

Product 1

HCID 19966720HCID 19966720, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

10.2 g of n-Butyl isocyanate (0.10 mol) were added dropwise at 25° C. to a suspension of 20.1 g of 2-(methylsulfinyl)benzenesulfonamide (0.09 mol) in 250 ml of acetonitrile. 13.9 g of potassium carbonate (0.10 mol) were added, after which the refluxing mixture was stirred for 4 hours. After cooling to 0° C., the mixture was poured onto 400 ml ice/water, brought to a pH of 1 by adding concentrated hydrochloric acid and extracted with methylene chloride. The organic extracts were washed neutral with water and dried. After removal of the solvent, 25 g of the title compound (85% of theory) were obtained as a pale brown oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed neutral with water
  3. customdried
  4. customAfter removal of the solvent

Sources & evidence

ORD record
ord-84a1378bc4434590a905e6536f070259
Source dataset
uspto-grants-1997_03
Patent number
US05612286

Reaction notes

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