Phosgene → HCID 13937616, compound

HRID 2118424Notes

Reaction equation

HRID 2118424 reaction equation
C(N[C:6]([NH:8][S:9]([CH2:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:11])=[O:10])=[O:7])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>>[CH3:25][O:24][C:22]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([N+:19]([O-:21])=[O:20])[C:13]=1[CH2:12][S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])=[O:23]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 13937615HCID 13937615, compound

Product 1

HCID 13937616HCID 13937616, compound

Procedure

A suspension of 8.4 g of the product from Example 5 and 0.1 g of 1,4-diazabicyclo[2.2.2]octane (DABCO) in 75 ml xylenes was heated to reflux temperatures. To this stirred solution was added 2 ml of phosgene at a rate that maintained the temperature above 130°. When the addition was complete, the turbid solution was heated at reflux temperature for 15 minutes, allowed to cool, and then filtered under an atmosphere of nitrogen. Removal of the solvent from the filtrate afforded the product as a viscous brown oil which was dissolved in dry methylene chloride and carried on to the next step without purification. The infrared spectrum of this intermediate displayed a characteristic isocyanate absorption at 2215 cm-1 and a carbonyl stretching absorption at 1730 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperatures
  3. temperaturemaintained the temperature above 130°
  4. additionWhen the addition
  5. temperaturethe turbid solution was heated
  6. temperatureat reflux temperature for 15 minutes
  7. temperatureto cool
  8. filtrationfiltered under an atmosphere of nitrogen
  9. customRemoval of the solvent from the filtrate

Sources & evidence

ORD record
ord-0edf0ae2aa0341bcb7b2bf85e8a84b87
Source dataset
uspto-grants-1987_07
Patent number
US04678500

Reaction notes

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