Ammonia → HCID 15868590, compound

HRID 1584707Notes

Reaction equation

HRID 1584707 reaction equation
[CH2:1]([CH:3]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1)=[O:7])[CH3:2].C(#[N:24])C.N>O>[CH2:1]([CH:3]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([S:14]([NH2:24])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1)=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6342AcetonitrileHCID 15868589HCID 15868589, compound

Product 1

HCID 15868590HCID 15868590, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ice-cooled solution of 460 g of 3-(2-ethylhexyloxycarbonyl)phenylsulfonyl chloride and 0.7 L of acetonitrile was added dropwise to 0.7 L of a 28% ammonia solution. The resultant mixture was stirred for 2 hours at room temperature. Thereafter, 0.7 L of water and 35 g of common salt were added thereto, followed by extraction with 1.0 L of ethyl acetate. The extract was washed with 0.5 L of diluted hydrochloric acid and 0.5 L of saturated brine and was then decolored with 20 g of active carbon. The active carbon was removed with Celite, and then the solvent was distilled off. 0.6 L of hexane was added and crystallized by cooling, and thus 338 g (1.08 mol, yield 77%) of 3-(2-ethylhexyloxycarbonyl)phenylsulfonamide was obtained m.p. 40° C. to 42° C.

Workup

  1. extractionfollowed by extraction with 1.0 L of ethyl acetate
  2. washThe extract was washed with 0.5 L of diluted hydrochloric acid and 0.5 L of saturated brine
  3. customThe active carbon was removed with Celite
  4. distillationthe solvent was distilled off
  5. addition0.6 L of hexane was added
  6. customcrystallized
  7. temperatureby cooling

Sources & evidence

ORD record
ord-2019ee5018334c3982f198a43ed870c2
Source dataset
uspto-grants-1999_08
Patent number
US05935757

Reaction notes

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