Water → HCID 21841991, compound

HRID 1737217Notes

Reaction equation

HRID 1737217 reaction equation
C[N:2](C)[NH:3][C:4]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5].Cl[C:19](Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.O.Cl[CH2:32][Cl:33]>>[Cl:33][C:32]1[N:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[C:4](=[O:5])[N:3]([CH3:19])[N:2]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 94429TriphosgeneHCID 21841973HCID 21841973, compound

Product 1

HCID 21841991HCID 21841991, compound

Conditions

Temperature
10 °C

Procedure

To a solution containing 61.5 g of the title compound of Step A dissolved in 1300 mL of dichloromethane under a nitrogen atmosphere was added 154 g of triphosgene portionwise with external cooling to maintain the reaction temperature at 0-20° C. The reaction mixture was then heated at reflux for approximately 24 h and then was cooled to 0° C. The reaction mixture was poured into water. The organic layer was separated and washed with water and saturated aqueous sodium chloride. The organic layer was then dried over magnesium sulfate, filtered and the filtrate was then evaporated to obtain 35.49 g of a white solid. This solid was purified by column chromatography on silica gel eluting with 2:1 hexane/ethyl acetate. Collection and evaporation of the fractions containing only the most polar component (according to thin layer chromatography on silica gel, 1:1 hexane/ethyl acetate mixture as the development solvent) yielded 12.2 g of the title compound of Step B as a white solid.

Workup

  1. temperaturewith external cooling
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for approximately 24 h
  4. temperaturewas cooled to 0° C
  5. customThe organic layer was separated
  6. washwashed with water and saturated aqueous sodium chloride
  7. dry with materialThe organic layer was then dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate was then evaporated

Sources & evidence

ORD record
ord-db0706700f2e4809ab3c98c82f96f1d9
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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