Phosgene → 5-Methyl-2-propargyloxyphenylsulfonylisocyanate

HRID 1248372Notes

Reaction equation

HRID 1248372 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-64db4a706b394d4c9eb593b03f43909f
Source dataset
uspto-grants-1985_06
Patent number
US04523944

Reaction notes

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