Phosgene → 2-(1-Methoxycarbonylethoxy)benzenesulfonyl isocyanate

HRID 1763064Notes

Reaction equation

HRID 1763064 reaction equation
[CH3:1][O:2][C:3]([CH:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15])[CH3:6])=[O:4].C(N=[C:23]=[O:24])CCC.C(Cl)(Cl)=O>N1(C2CCCCCCC2)CCCCCCN1.C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]=[C:23]=[O:24])(=[O:16])=[O:15])[CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 6371Phosgene2×HCID 8110Butyl isocyanateHCID 221528372-(1-Methoxycarbonylethoxy)benzenesulfonamide

Product 1

HCID 221528362-(1-Methoxycarbonylethoxy)benzenesulfonyl isocyanateYield 125.5%

Reagents, catalysts & solvents 2

HCID 66583054DiazabicyclooctaneCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 12.9 g of 2-(1-methoxycarbonylethoxy)benzenesulfonamide, 4.9 g of n-butylisocyanate and 0.1 g of diazabicyclooctane and 130 ml of xylene is refluxed for 30 minutes. Then 10 g of phosgene are passed into the solution at the same temperature over 90 minutes. Excess phosgene is expelled with nitrogen and the solution is then cooled and concentrated in vacuo, affording 17.7 g of 2-(1-methoxycarbonylethoxy)benzenesulfonyl isocyanate in the form of a brownish oil which can be further used without purification.

Workup

  1. temperatureis refluxed for 30 minutes
  2. temperaturethe solution is then cooled
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-681145b2c1c947b78a51ce1c1ff24f35
Source dataset
uspto-grants-1989_05
Patent number
US04835311

Reaction notes

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