Hydrochloric Acid → 4-(2,4-Dioxo-8-oxa-1,3-diazaspiro[4.5]decan-3-yl)-2-(trifluoromethyl)-benzonitrile

HRID 264012Notes

Reaction equation

HRID 264012 reaction equation
N=[C:2]1[C:6]2([CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[NH:5][C:4](=[O:12])[N:3]1[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=1.C[OH:26].C(Cl)(Cl)Cl.Cl>O>[O:12]=[C:4]1[N:3]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:22])[F:23])[CH:14]=2)[C:2](=[O:26])[C:6]2([CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[NH:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6212ChloroformHCID 153454974-(4-Imino-2-oxo-8-oxa-1,3-diazaspiro[4.5]decan-3-yl)-2-(trifluoromethyl)-benzonitrile

Product 1

HCID 153454984-(2,4-Dioxo-8-oxa-1,3-diazaspiro[4.5]decan-3-yl)-2-(trifluoromethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.66 g of the product of Example 1 were introduced into 30 ml of methanol, 10 ml of chloroform and 10 ml of 2N hydrochloric acid, and the mixture was refluxed for 50 minutes. 100 ml of water were added and extraction was carried out 3 times with ethyl acetate. The organic phase was washed with salt water, dried and purified on silica with methylene chloride-acetone: 85-15 as eluant. The resultant product was dissolved in 100 ml of isopropanol at about 70° C. and filtration was carried out, followed by concentrating, ice-cooling for one hour, separating and drying to obtain 1,425 g of the expected product (white crystals) melting at 192°-193° C.

Workup

  1. temperaturethe mixture was refluxed for 50 minutes
  2. extractionextraction
  3. washThe organic phase was washed with salt water
  4. customdried
  5. custompurified on silica with methylene chloride-acetone
  6. dissolutionThe resultant product was dissolved in 100 ml of isopropanol at about 70° C.
  7. filtrationfiltration
  8. concentrationby concentrating
  9. temperatureice-cooling for one hour
  10. customseparating
  11. customdrying

Sources & evidence

ORD record
ord-7e54de2010ea4ce284f3795e12877156
Source dataset
uspto-grants-1997_07
Patent number
US05646172

Reaction notes

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