Dabco → 2-Phenoxybenzene-1-sulfonyl isocyanate

HRID 746146Notes

Reaction equation

HRID 746146 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N=[C:25]=[O:26])CCCCC.N12CCN(CC1)CC2.ClC(OC(Cl)(Cl)Cl)=O>C1(C)C(C)=CC=CC=1>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]=[C:25]=[O:26])(=[O:15])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 9237DabcoHCID 10426DiphosgeneHCID 75659Hexyl isocyanateHCID 155615762-Phenoxybenzene-1-sulfonamide

Product 1

HCID 131370512-Phenoxybenzene-1-sulfonyl isocyanateYield 82.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

25.0 g of 2-phenoxyphenylsulfonamide, 14.0 g of n-hexyl isocyanate, a catalytic amount of 1,4-diazabicyclo-[2,2,2]-octane and 150 ml xylene were refluxed with stirring for an hour. Thereafter, the mixture was reacted with a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene in a manner similar to that of Example (1). At the end of the reaction, the xylene and n-hexyl isocyanate were distilled off, to obtain 22.8 g of 2-phenoxyphenylsulfonylisocyanate. B.p. 146°-150° C./0.7 mmHg.

Workup

  1. customAt the end of the reaction
  2. distillationthe xylene and n-hexyl isocyanate were distilled off

Sources & evidence

ORD record
ord-d2123c49c01d4a1f9e676fef106557e0
Source dataset
uspto-grants-1986_07
Patent number
US04602941

Reaction notes

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