Butyl isocyanate → HCID 13686314, compound

HRID 1731252Notes

Reaction equation

HRID 1731252 reaction equation
[CH3:1][N:2]1[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:4]=2[S:3]1(=[O:16])=[O:15].[CH2:17]([N:21]=[C:22]=[O:23])[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.CCOCC>[CH2:17]([NH:21][C:22]([NH:14][S:11]([C:10]1[C:4]2[S:3](=[O:16])(=[O:15])[N:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)(=[O:12])=[O:13])=[O:23])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium Carbonate2×HCID 13686313HCID 13686313, compound

Product 1

HCID 13686314HCID 13686314, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 13.0 g of 2-methyl-2,3-dihydro-1,2-benzisothiazole-7-sulfonamide-1,1-dioxide, 11.2 ml of butyl isocyanate and 13.8 g of potassium carbonate in 200 ml of dry methyl ethyl ketone was heated at reflux for 2 hours. 13.8 g of potassium carbonate was added and heating was continued for an additional 16 hours. The mixture was cooled, the solvent was decanted from the solids, concentrated in vacuo, the residue dissolved in ethyl acetate and washed with saturated aq. NaHCO3. The aqueous wash was added to the original solids diluted with water and acidified to pH ~3 with dilute HCl. The mixture was extracted with methylene chloride, the extract was washed with water and brine, dried and concentrated in vacuo leaving a solid which was slurried in ether and filtered to give 13.24 g of the title compound as a white powder, m.p. 162°-164° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureheating
  4. temperatureThe mixture was cooled
  5. customthe solvent was decanted from the solids
  6. concentrationconcentrated in vacuo
  7. dissolutionthe residue dissolved in ethyl acetate
  8. washwashed with saturated aq. NaHCO3
  9. washThe aqueous wash
  10. additionwas added to the original solids
  11. additiondiluted with water
  12. extractionThe mixture was extracted with methylene chloride
  13. washthe extract was washed with water and brine
  14. customdried
  15. concentrationconcentrated in vacuo
  16. customleaving a solid which
  17. filtrationfiltered

Sources & evidence

ORD record
ord-927d8e1e1da54e96bcd566a76702820e
Source dataset
uspto-grants-1986_11
Patent number
US04620870

Reaction notes

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