Butyl isocyanate → HCID 14501045, compound

HRID 230990Notes

Reaction equation

HRID 230990 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[C:10]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31]([N:35]=[C:36]=[O:37])[CH2:32][CH2:33][CH3:34]>C(#N)C>[CH2:31]([NH:35][C:36]([NH:14][S:11]([C:10]1[N:9]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[O:13])=[O:12])=[O:37])[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 14052417HCID 14052417, compound

Product 1

HCID 14501045HCID 14501045, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6 g of 4-ethoxycarbonyl-1-(2-quinolyl)pyrazole-5-sulfonamide and 3.6 g of anhydrous potassium carbonate dissolved in 40 ml of acetonitrile, was added 1.9 g of n-butylisocyanate at room temperature, followed by heating under reflux for 1.5 hours. After the reaction was completed, acetonitrile was evaporated under reduced pressure, and then the residue was poured into ice water to filter insolubles off, and then the filtrate was precipitated with hydrochloric acid. Crystals precipitated were filtered, washed with water and dried to obtain 7 g of N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-(2-quinolyl)pyrazole-5-sulfonamide. m.p: 140° to 142° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. customacetonitrile was evaporated under reduced pressure
  4. additionthe residue was poured into ice water
  5. filtrationto filter insolubles off, and then the filtrate
  6. customwas precipitated with hydrochloric acid
  7. customCrystals precipitated
  8. filtrationwere filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-583d132bd39a4a23a46450d2f87e6d2a
Source dataset
uspto-grants-1989_07
Patent number
US04844728

Reaction notes

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