Phosgene → 2-Biphenylylsulfanylisocyanate

HRID 279733

Reaction equation

HRID 279733 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH2:10])(=O)=O.C(N=[C:22]=[O:23])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>ClC1C=CC=CC=1>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][N:10]=[C:22]=[O:23]

Participants

6

Reactant 4

HCID 6371Phosgene3×HCID 8110Butyl isocyanateHCID 9237DabcoHCID 123715202-Phenylbenzene-1-sulfonamide

Product 1

HCID 233223832-Biphenylylsulfanylisocyanate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfanylisocyanate, B.p 135°-137° C./0.7-0.8 mmHg.

Workup

  1. temperaturewhile maintaining the internal temperature at 115°-120° C
  2. stirringthe reaction mixture was further stirred at the reflux temperature for a short time
  3. customthe reaction
  4. temperatureThe mixture was cooled
  5. filtrationif necessary, it was filtered under reduced pressure
  6. customto remove the insoluble matter
  7. concentrationIt was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b803ebad71d248dab033f98c2b32ba6c
Source dataset
uspto-grants-1986_05
Patent number
US04586951

Linked notes

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