Ammonia → HCID 19020738, compound

HRID 1109519Notes

Reaction equation

HRID 1109519 reaction equation
Cl[C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][N:16]([CH2:18][CH:19]([OH:22])CO)[C:15](=[O:23])[C:14]=2[CH:24]=1.C([N:27](CC)CC)C.N>O1CCCC1>[C:2]([O:4][CH2:5][CH:19]([OH:22])[CH2:18][N:16]1[C:15](=[O:23])[C:14]2[CH:24]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=2[O:17]1)(=[O:3])[NH2:27]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10426DiphosgeneHCID 15630456HCID 15630456, compound

Product 1

HCID 19020738HCID 19020738, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.40 g of trichloromethyl chloroformate was added to a solution of 1.00 g of 5-chloro-2-(2,3-dihydroxypropyl)-1,2-benzisoxazol-3-one (prepared as disclosed in Japanese Patent Application Kokai No. Sho. 55-83766) in 20 ml of dry tetrahydrofuran and the mixture was then stirred at room temperature for 30 minutes. After this, 0.42 g of triethylamine was added dropwise at 5° C., and the mixture was again stirred at the same temperature for 30 minutes. At the end of this time, 5.0 ml of 28% v/v aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. It was then heated under reflux for an additional 3 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate, washed with a 10% w/v aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, eluted with ethyl acetate, to give 0.75 g (yield 64.1%) of the title compound as a colorless powder, melting at 161°-162° C.

Workup

  1. stirringthe mixture was again stirred at the same temperature for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. temperatureIt was then heated
  4. temperatureunder reflux for an additional 3 hours
  5. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  6. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
  7. washwashed with a 10% w/v aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customthe residue was purified by column chromatography through silica gel
  11. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-7a36173c6fe34ce49421c517dabffd60
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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