Butyl isocyanate → HCID 13489816, compound

HRID 1980776Notes

Reaction equation

HRID 1980776 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([NH2:15])(=[O:14])=[O:13])=[CH:4][CH:3]=[N:2]1.[CH2:16]([N:20]=[C:21]=[O:22])[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([NH:20][C:21]([NH:15][S:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[O:1][N:2]=[CH:3][CH:4]=1)(=[O:13])=[O:14])=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 134898132-(5-Isoxazolyl)benzenesulfonamide

Product 1

HCID 13489816HCID 13489816, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 8.7 g of 2-(isoxazol-5-yl)benzenesulfonamide prepared in Example 5, 4.7 g of n-butyl isocyanate and 5.4 g of potassium carbonate in 125 ml of 2-butanone was refluxed for 7 hours. The resulting suspension was concentrated to dryness in vacuo. The residue was taken up in 200 ml of water and extracted once with 100 ml of ethyl ether. The aqueous layer was acidified with 2N HCl and the resulting suspension was extracted with methylene chloride. After drying the methylene chloride extract over sodium sulfate, the solvent was evaporated off under reduced pressure. The solid residue was recrystallized from acetonitrile to give 10 g of the title compound; m.p. 110°-113° C.

Workup

  1. concentrationThe resulting suspension was concentrated to dryness in vacuo
  2. extractionextracted once with 100 ml of ethyl ether
  3. extractionthe resulting suspension was extracted with methylene chloride
  4. dry with materialAfter drying the methylene chloride
  5. extractionextract over sodium sulfate
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe solid residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b0a98ca01eb4415b9698165eb243df13
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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