Phosgene → 5-Methyl-2-propargyloxyphenylsulfonylisocyanate

HRID 325801Notes

Reaction equation

HRID 325801 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]#[CH:15])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.C(N=[C:21]=[O:22])CCC.C(Cl)(Cl)=O>N12CCN(CC1)CC2.C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]#[CH:15])=[C:6]([S:8]([N:11]=[C:21]=[O:22])(=[O:9])=[O:10])[CH:7]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 134729485-Methyl-2-propargyloxyphenylsulfonamide

Product 1

HCID 134729535-Methyl-2-propargyloxyphenylsulfonylisocyanateYield 112.5%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 22.4 g of 5-methyl-2-propargyloxyphenylsulfonamide, 9.9 g of n-butylisocyanate, 0.3 g of 1,4-diazabicyclo(2,2,2)octane and 350 ml of absolute xylene is refluxed for 30 minutes; and about 20 g of phosgene are subsequently introduced at 115°-120° C. during 2 hours. After the excess of phosgene has been removed from the reaction mixture by feeding in nitrogen, the mixture is cooled to room temperature, filtered, and concentrated in vacuo. There is thus obtained as crude product 28.1 g of 5-methyl-2-propargyloxyphenylsulfonylisocyanate in the form of brown oil. This crude product is used, without further purification, in the subsequent stage.

Workup

  1. temperatureis refluxed for 30 minutes
  2. customAfter the excess of phosgene has been removed from the reaction mixture
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0610f23b07414a1887e4b5a6b1f875ee
Source dataset
uspto-grants-1984_04
Patent number
US04443243

Reaction notes

Loading…