Phosgene → HCID 13472237, compound

HRID 1789128Notes

Reaction equation

HRID 1789128 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([NH2:13])(=[O:12])=[O:11])[C:4]=2[CH2:3][O:2]1.C(N=[C:19]=[O:20])CCC.C1N2CCN(CC2)C1.C(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([N:13]=[C:19]=[O:20])(=[O:11])=[O:12])[C:4]=2[CH2:3][O:2]1

Participants

6

Reactant 4

HCID 6371Phosgene2×HCID 8110Butyl isocyanateHCID 9237DabcoHCID 13472236HCID 13472236, compound

Product 1

HCID 13472237HCID 13472237, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 7.0 g of 1,3-dihydrobenzo[c]furan-4-sulfonamide, 4.0 ml of butyl isocyanate, 0.1 g of DABCO® and 150 ml xylene was heated to reflux. Phosgene (3.1 ml) was added in small portions to the reaction mixture while maintaining the reaction temperature <130°. When addition of phosgene was complete, the reaction mixture was heated to reflux (128°) for 1 hour, then cooled under nitrogen. The reaction mixture was filtered under nitrogen, and the filtrate was concentrated in vacuo to give 1,3-dihydrobenzo[c]furan-4-sulfonyl isocyanate as an amber oil. The crude sulfonyl isocyanate was dissolved in methylene chloride (total volume=28 ml) for reaction with amino heterocycles.

Workup

  1. temperaturewas heated to reflux
  2. temperaturewhile maintaining the reaction temperature <130°
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux (128°) for 1 hour
  5. temperaturecooled under nitrogen
  6. filtrationThe reaction mixture was filtered under nitrogen
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cc092392aa584ae0992038eb02f92cc7
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

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