Phosgene → 4-Methyl-3-thiophenesulfonyl isocyanate

HRID 434594Notes

Reaction equation

HRID 434594 reaction equation
C(N[C:6]([NH:8][S:9]([C:12]1[C:16]([CH3:17])=[CH:15][S:14][CH:13]=1)(=[O:11])=[O:10])=[O:7])CCC.C1(C2CCCCCCC2)CCCCCCC1.C(Cl)(Cl)=O>>[CH3:17][C:16]1[C:12]([S:9]([N:8]=[C:6]=[O:7])(=[O:10])=[O:11])=[CH:13][S:14][CH:15]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 524587BicyclooctylHCID 13203330N-(Butylcarbamoyl)-4-methylthiophene-3-sulfonamide

Product 1

HCID 132033314-Methyl-3-thiophenesulfonyl isocyanate

Procedure

A mixture of 18.8 g of N-butylaminocarbonyl-4-methyl-3-thiophenesulfonamide, 0.3 g of 1,4-diaza[2.2.2.]bicyclooctane and 100 ml of dry xylenes was heated to reflux (136° C.) and 7.4 g of phosgene was then added at a rate to maintain the temperature at above 125°. The mixture was refluxed for three and one half hours after the addition was completed. It was then cooled, filtered and concentrated in vacuo to yield a dark oil, (15 g) which showed absorption in the infrared spectrum at 2250 cm-1. This intermediate was used without further purification.

Workup

  1. additionwas then added at a rate
  2. temperatureto maintain the temperature at above 125°
  3. temperatureThe mixture was refluxed for three and one half hours
  4. additionafter the addition
  5. temperatureIt was then cooled
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a dark oil, (15 g) which
  9. customabsorption in the infrared spectrum at 2250 cm-1
  10. customThis intermediate was used without further purification

Sources & evidence

ORD record
ord-8db3c2d2592a42c692bbdd1b005f5eaf
Source dataset
uspto-grants-1983_08
Patent number
US04398939

Reaction notes

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