Phosgene → HCID 20456547, compound

HRID 904777Notes

Reaction equation

HRID 904777 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([S:12]([NH2:15])(=[O:14])=[O:13])[CH3:11])([O-:3])=[O:2].C(N=[C:21]=[O:22])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([S:12]([N:15]=[C:21]=[O:22])(=[O:13])=[O:14])[CH3:11])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 9237DabcoHCID 13282658HCID 13282658, compound

Product 1

HCID 20456547HCID 20456547, compound

Procedure

A mixture of 16 g of the product from Example 14, 8.0 ml of n-butyl isocyanate, and 0.2 g of 1,4-diazabicyclo[2.2.2]octane (DABCO) in 125 ml dry xylenes was heated to 130°-135° C. for 11/2 hours. To this solution was added 6 ml of phosgene at a rate which maintained the temperature above 130° C. After completion of the addition (ca. one hour), the solution was cooled and filtered under nitrogen. The filtrate was concentrated in vacuo to give the crude 1-(2-nitrophenyl)ethanesulfonyl isocyanate as a viscous orange oil. The IR spectrum of this compound displayed a characteristic isocyanate absorption at 2240 cm-1.

Workup

  1. temperaturewas heated to 130°-135° C. for 11/2 hours
  2. temperaturemaintained the temperature above 130° C
  3. additionAfter completion of the addition (ca. one hour)
  4. temperaturethe solution was cooled
  5. filtrationfiltered under nitrogen
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-13c74eb266454ae1b03dfb6d8143d13c
Source dataset
uspto-grants-1983_12
Patent number
US04420325

Reaction notes

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