Phosgene → HCID 13852723, compound

HRID 619899Notes

Reaction equation

HRID 619899 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])(=[O:11])=[O:10])=[O:7])CCC.C(Cl)(Cl)=O>>[CH3:23][CH:21]([S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([N:8]=[C:6]=[O:7])(=[O:10])=[O:11])(=[O:20])=[O:19])[CH3:22]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 13852722HCID 13852722, compound

Product 1

HCID 13852723HCID 13852723, compound

Procedure

A solution of N-[butylaminocarbonyl]-2-[(1-methylethyl)sulfonyl]benzenesulfonamide (17.4 g, 0.048 mol) and 1.4-diaza[2,2,2]bicyclooctane (0.1 g) in mixed xylenes (90 ml) was heated to 135°-140°. Liquid phosgene (3.6 ml, 0.050 mol) was added at a rate to maintain an internal temperature between 125°-135°. When the addition was complete, the solution was refluxed for 2 hours, cooled to room temperature and then filtered under a nitrogen atmosphere. Removal of solvent in vacuo gave 2-[(1-methylethyl)sulfonyl]benzenesulfonyl isocyanate, which was used immediately without further purification.

Workup

  1. temperatureto maintain an internal temperature between 125°-135°
  2. additionWhen the addition
  3. temperaturethe solution was refluxed for 2 hours
  4. filtrationfiltered under a nitrogen atmosphere
  5. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-c0bc37df0d6746a9a6002424bfee7ecd
Source dataset
uspto-grants-1989_04
Patent number
US04818277

Reaction notes

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