Phosgene → HCID 20143943, compound

HRID 2118432Notes

Reaction equation

HRID 2118432 reaction equation
C(N[C:6]([NH:8][S:9]([CH2:12][C:13]1[C:22]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:11])=[O:10])=[O:7])CCC.N12CCN(CC1)CC2.C(Cl)(Cl)=O>>[CH3:27][N:26]([S:23]([C:22]1[CH:21]=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]=1[CH2:12][S:9]([N:8]=[C:6]=[O:7])(=[O:11])=[O:10])(=[O:25])=[O:24])[CH3:28]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 139376452-[[[(n-Butyl)aminocarbonyl]aminosulfonyl]methyl]-3-(N,N-dimethylamino)sulfonylbenzoic acid, methyl ester

Product 1

HCID 20143943HCID 20143943, compound

Procedure

A suspension of 7.4 g of the product from Example 15 and 0.1 g of 1,4-diazabicyclo[2.2.2]octane in 100 ml xylenes was heated to reflux temperature. To this solution was added 1.5 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 about one hour, allowed to cool, and then filtered under an atmosphere of nitrogen. Removal of the solvent from the filtrate gave the product as a dark 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 2240 cm-1.

Workup

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

Sources & evidence

ORD record
ord-a526caeb438b441296c8ee4669a0c2fc
Source dataset
uspto-grants-1987_07
Patent number
US04678500

Reaction notes

Loading…