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

HRID 619199
Notes
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Reaction equation

HRID 619199 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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-a3bb17ea1521463d816e3931da9452fa
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958936

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes