Phosgene → HCID 13489817, compound

HRID 1193444Notes

Reaction equation

HRID 1193444 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:22][N:21]=[CH:20][CH:19]=1)(=[O:11])=[O:10])=[O:7])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[O:22]1[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])=[CH:19][CH:20]=[N:21]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13489816HCID 13489816, compound

Product 1

HCID 13489817HCID 13489817, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 6 g of N-(butylaminocarbonyl)-2-(isoxazol-5-yl)benzenesulfonamide, prepared in Example 6, in 50 ml of xylene containing 0.2 g of DABCO was heated at 130°-135° C. while 1.6 ml of phosgene was added portionwise at a rate to maintain a reflux temperature of 130°-135° C. The mixture was refluxed for an additional 2 hours, cooled under nitrogen to room temperature, filtered, and the filtrate was concentrated to dryness in vacuo. A sample of the crude oily product displayed a characteristic sulfonyl isocyanate band in the IR at 2200 cm-1.

Workup

  1. additionwas added portionwise at a rate
  2. temperatureto maintain a reflux temperature of 130°-135° C
  3. temperatureThe mixture was refluxed for an additional 2 hours
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-6eddeb059e1b41aab4a1289636c14e0a
Source dataset
uspto-grants-1989_03
Patent number
US04810282

Reaction notes

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