Butyl isocyanate → HCID 13364390, compound

HRID 1031341Notes

Reaction equation

HRID 1031341 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:15])[C:10]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25]>CC(C)=O>[CH2:22]([NH:26][C:27]([NH:14][S:11]([C:10]1[N:9]([CH3:15])[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[O:13])=[O:12])=[O:28])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 13364389Ethyl 1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylate

Product 1

HCID 13364390HCID 13364390, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 5.0 g of4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide(Reference example 25), 4.45 g of dry potassium carbonate and 50 ml of acetone was added 2.13 g of n-butyl isocyanate at room temperature, and the mixture was stirred under reflux for 3 hours. After the reaction, acetone was evaporated under reduced pressure, and ice-water was added to the residue, followed by filtration of the insolubles. The filtrate was made acidic with hydrochloric acid and the crystals precipitated were filtered, washed with water and dried to give 5.1 g of N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide melting at 117°-119° C. Then, this product was added into 120 ml of dry toluene, and 9.1 g of phosgene was passed into the mixture under reflux, followed further by refluxing for 1.5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain crude sulfonyl isocyanate.

Workup

  1. temperatureunder reflux for 3 hours
  2. customwas evaporated under reduced pressure, and ice-water
  3. additionwas added to the residue
  4. filtrationfollowed by filtration of the insolubles
  5. customthe crystals precipitated
  6. filtrationwere filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7ba8b4ad927e4146a5260aa511430f8a
Source dataset
uspto-grants-1990_09
Patent number
US04954164

Reaction notes

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