Phosgene → 2-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonyl isocyanate

HRID 34877Notes

Reaction equation

HRID 34877 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:19][C:20](=[O:24])[N:21]([CH3:23])[N:22]=1)(=[O:11])=[O:10])=[O:7])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[CH3:23][N:21]1[C:20](=[O:24])[O:19][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])=[N:22]1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13958860N-[(Butylamino)carbonyl]-2-(4,5-dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonamide

Product 1

HCID 139588612-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonyl isocyanateYield 108.7%

Procedure

A suspension of 8 g of the product of Example 7 and 0.4 g of DABCO in 90 ml of xylenes was heated under N2 at 130°-135° C. while 1.8 ml of phosgene was added portionwise at a rate to maintain a reflux temperature of about 130°-135° C. The mixture was refluxed an additional two hours, cooled under N2 to room temperature, filtered, and the filtrate was concentrated in vacuo to yield 6.9 g of the subject compound as a crude oil.

Workup

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

Sources & evidence

ORD record
ord-cad2be3f15de4c6eaa93a331efc5ead5
Source dataset
uspto-grants-1988_08
Patent number
US04764205

Reaction notes

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