Phosgene → 2-(1-Cyclopentenyl)benzenesulfonyl Isocyanate

HRID 1164182Notes

Reaction equation

HRID 1164182 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([NH2:15])(=[O:14])=[O:13])[CH2:5][CH2:4][CH2:3][CH:2]=1.C(N=[C:21]=[O:22])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>>[C:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([N:15]=[C:21]=[O:22])(=[O:13])=[O:14])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 130973812-(1-Cyclopentenyl)benzenesulfonamide

Product 1

HCID 130973822-(1-Cyclopentenyl)benzenesulfonyl Isocyanate

Procedure

A solution of 2.5 g of 2-(1-cyclopentenyl)benzenesulfonamide in 20 ml of xylenes was contacted with 1.4 g of n-butylisocyanate and a trace amount (ca. 20 mg) of DABCO then heated to reflux of 139°. Liquified phosgene (1.2 ml) was then added thereby reducing the temperature and reflux continued until the boiling point of the mixture stopped rising towards the original 139° (ca. 15 min. required), which indicated a complete reaction. The solution was then evaporated under reduced pressure to yield an oil. The infrared spectrum exhibited the characteristic 2220 cm-1 band indicating the presence of the title compound which was used directly.

Workup

  1. temperatureto reflux of 139°
  2. temperaturereflux
  3. customstopped rising towards the original 139° (ca. 15 min. required), which
  4. customa complete reaction
  5. customThe solution was then evaporated under reduced pressure
  6. customto yield an oil

Sources & evidence

ORD record
ord-ac9788dfa0154cf990cde3abd275a88e
Source dataset
uspto-grants-1983_01
Patent number
US04368069

Reaction notes

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