Butyl isocyanate → HCID 53796829, compound

HRID 985893Notes

Reaction equation

HRID 985893 reaction equation
[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH2:15])(=[O:14])=[O:13])=[CH:3][Cl:4].[CH2:16]([N:20]=[C:21]=[O:22])[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:16]([NH:20][C:21]([NH:15][S:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][C:2]([Cl:1])=[CH:3][Cl:4])(=[O:13])=[O:14])=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 537128512-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonamide

Product 1

HCID 53796829HCID 53796829, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1,2-Dichloroethen-1-yloxy)benzenesulfonamide (13.4 g), 12.4 g of n-butyl isocyanate and 15.2 g of anhydrous potassium carbonate were combined in 200 ml of dry tetrahydrofuran and heated to reflux for three hours. The mixture was then cooled to room temperature, filtered and the solvent removed by evaporation. The residue and precipitate were recombined and dissolved in 600 ml of water and the mixture acidified with 10% hydrochloric acid. The resultant precipitate was removed by filtration, washed with water, air dried and then washed with hexane. After drying in vacuo at 80° overnight, 13.65 g of solid product melting at 122°-125° was obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. dissolutiondissolved in 600 ml of water
  6. customThe resultant precipitate was removed by filtration
  7. washwashed with water, air
  8. customdried
  9. washwashed with hexane
  10. customAfter drying in vacuo at 80° overnight

Sources & evidence

ORD record
ord-ea317ff6b9e649fb9180860f9ae23820
Source dataset
uspto-grants-1987_12
Patent number
USH0000386

Reaction notes

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