Phosgene → 2-(Dimethylaminosulfonyloxy)benzenesulfonyl isocyanate

HRID 462332Notes

Reaction equation

HRID 462332 reaction equation
[CH3:1][N:2]([CH3:17])[S:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14])(=[O:5])=[O:4].CCCCN=[C:23]=[O:24].C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[CH3:1][N:2]([CH3:17])[S:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([N:16]=[C:23]=[O:24])(=[O:15])=[O:14])(=[O:4])=[O:5]

Participants

5

Reactant 4

HCID 6371Phosgene2×HCID 8110Butyl isocyanateHCID 9237DabcoHCID 134731262-(Dimethylaminosulfonyloxy)benzenesulfonamide

Product 1

HCID 134731272-(Dimethylaminosulfonyloxy)benzenesulfonyl isocyanate

Procedure

To 6.0 g (0.021 mole) 2-(dimethylaminosulfonyloxy)benzenesulfonamide suspended in 75 ml dry xylenes was added 2.1 g (0.021 mole) N-butyl isocyanate and a catalytic amount of 1,4-diazobicyclo[2.2.2]octane (~0.05 g). This mixture was rapidly heated to reflux temperature (~135° C.) and 3.0 ml of phosgene was slowly added (at such a rate as to keep the reaction temperature greater than 128° C.). The phosgene addition required ~3 hours. The reaction was cooled to room temperature, filtered under N2, and the solvent evaporated under reduced pressure. The infrared spectrum of the resultant oil was consistent for 2-(dimethylaminosulfonyloxy)benzenesulfonyl isocyanate, (2240 cm-1).

Workup

  1. temperatureThis mixture was rapidly heated
  2. additionwas slowly added (at such a rate as
  3. customthe reaction temperature greater than 128° C.
  4. filtrationfiltered under N2
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d8f4f7a484a64e82b7d44dff39b9e9f4
Source dataset
uspto-grants-1985_05
Patent number
US04515624

Reaction notes

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