Phosgene → 2-Chloro-6-phenylbenzenesulfonyl Isocyanate

HRID 236232Notes

Reaction equation

HRID 236232 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:24])(=[O:11])=[O:10])=[O:7])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[Cl:24][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]=1[S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13852353N-(Butylaminocarbonyl)-2-chloro-6-phenylbenzenesulfonamide

Product 1

HCID 138523542-Chloro-6-phenylbenzenesulfonyl Isocyanate

Procedure

A mixture of 9.5 g (0.026 mol) of N-(butylaminocarbonyl)-2-chloro-6-phenylbenzenesulfonamide of Example 3 and 0.02 g DABCO was heated in 120 ml dry xylenes to reflux (138°) with a short water condenser and dry ice cold finger condenser attached. An excess of phosgene gas was introduced and reflux was continued for 2 hours. The mixture was then cooled, filtered under nitrogen atmosphere then evaporated to an amber oil, 8.5 g. An infrared spectrum exhibited an absorption at 2250 cm-1 indicating the title compound.

Workup

  1. temperatureto reflux (138°) with a short water condenser and dry ice cold finger condenser
  2. temperaturereflux
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered under nitrogen atmosphere
  5. customthen evaporated to an amber oil, 8.5 g
  6. customan absorption at 2250 cm-1

Sources & evidence

ORD record
ord-3a451d6b749a40159990a86891c90b8d
Source dataset
uspto-grants-1987_02
Patent number
US04643761

Reaction notes

Loading…