Ammonia → HCID 19020721, compound

HRID 1109516Notes

Reaction equation

HRID 1109516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([O:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC([O:22][C:23](Cl)(Cl)Cl)=O.C([N:29](CC)CC)C.N>O1CCCC1>[C:23]([O:17][CH2:16][CH:15]([OH:18])[CH2:14][O:13][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)(=[O:22])[NH2:29]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10426DiphosgeneHCID 19020727HCID 19020727, compound

Product 1

HCID 19020721HCID 19020721, compoundYield 132.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (37.0 mmoles) of 5-(m-chlorophenyl)-3-(2,3-dihydroxypropoxy)isoxazole [prepared as described in step (a) above] in 300 ml of dry tetrahydrofuran was cooled to 5° C., and then 3.96 g (20.0 mmoles) of trichloromethyl chloroformate were added dropwise to the mixture. The mixture was then stirred at 5°-6° C. for 30 minutes. At the end of this time, 4.04 g (40.0 mmoles) of triethylamine were added dropwise to the mixture at 5°-10° C., and the mixture was stirred at 3°-5° C. for 1 hour. 50 ml (400.0 mmoles) of 28% v/v aqueous ammonia were then added at one time, and the mixture was stirred at room temperature for a further 18 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was diluted with 400 ml of ethyl acetate. The mixture was then washed with 400 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation under reduced pressure to give a solid residue. This solid residue was recrystallized from ethyl acetate, to give 8.30 g (yield 72.1%) of the title compound as colorless scales, melting at 149°-150° C.

Workup

  1. stirringthe mixture was stirred at 3°-5° C. for 1 hour
  2. stirringthe mixture was stirred at room temperature for a further 18 hours
  3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  4. additionthe resulting residue was diluted with 400 ml of ethyl acetate
  5. washThe mixture was then washed with 400 ml of a 10% w/v aqueous solution of sodium chloride
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe desiccant was removed by filtration
  8. customthe solvent was removed by distillation under reduced pressure
  9. customto give a solid residue
  10. customThis solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0b95d0ff327d4299a2d01de65c176691
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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