Butyl isocyanate → 2-Biphenylylsulfonylisocyanate

HRID 615529

Reaction equation

HRID 615529 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:9])=[O:8].C(N=[C:22]=[O:23])CCC.N12CCN(CC1)CC2.ClC(OC(Cl)(Cl)Cl)=O>C1(C)C(C)=CC=CC=1>[C:1]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([N:10]=[C:22]=[O:23])(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 8110Butyl isocyanateHCID 9237DabcoHCID 10426DiphosgeneHCID 123715202-Phenylbenzene-1-sulfonamide

Product 1

HCID 131033202-BiphenylylsulfonylisocyanateYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

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 150 ml of xylene were refluxed with stirring for an hour. Then, a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene was added dropwise over 2.5 hours while maintaining the internal temperature at 120°-125° C. After this addition, the mixture was held at this temperature for a while, and thereafter the mixture was refluxed for a short period to complete the reaction. At the end of the reaction, the xylene and n-butyl isocyanate were distilled off under reduced pressure, to obtain 22.0 g of 2-biphenylylsulfonylisocyanate of high purity. B.pt. 135°-137° C./0.7-0.8 mmHg.

Workup

  1. temperaturewhile maintaining the internal temperature at 120°-125° C
  2. additionAfter this addition
  3. temperaturethe mixture was refluxed for a short period
  4. customthe reaction
  5. customAt the end of the reaction
  6. distillationthe xylene and n-butyl isocyanate were distilled off under reduced pressure

Sources & evidence

ORD record
ord-038007230513477d8ac92249f5e9abc3
Source dataset
uspto-grants-1985_02
Patent number
US04500342

Linked notes

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