Butyl isocyanate → HCID 13686314, compound

HRID 1607788Notes

Reaction equation

HRID 1607788 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 originalsolids diluted with water and acidified to pH ~3 with dilute HCl. Themixture was extracted with methylene chloride, the extract was washed with water and brine, dried and concentrated in vacuo leaving a solid which wasslurried 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 originalsolids
  11. additiondiluted with water
  12. extractionThemixture 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-01720512b8fd42e2aa32ae6d9bd031e3
Source dataset
uspto-grants-1989_09
Patent number
US04867781

Reaction notes

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