Benzene → HCID 178505358, compound

HRID 1700676Notes

Reaction equation

HRID 1700676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[N:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[C:11]=2[C:10](=O)[CH2:9]1.[C:23]([NH:26][NH2:27])([NH2:25])=[NH:24].Cl.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].C1C=CC=CC=1>C(O)C>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[N:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[C:11]=2[C:10](=[N:27][NH:26][C:23]([NH2:25])=[NH:24])[CH2:9]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6395Methanesulfonic AcidHCID 183176067-(2-Chlorophenyl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178505358HCID 178505358, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(2-chlorophenyl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-one (0.335 g) and aminoguanidine hydrochloride (165 mg) in ethanol (10 ml) were added methanesulfonic acid (0.3 ml) and benzene (10 ml), and the mixture was refluxed for 80 minutes. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution to make the solution alkaline. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was dissolved in acetone, and to the solution was added methanesulfonic acid (0.15 ml). Precipitated crystals were filtered, washed with acetone and dried to give 7-(2-chlorophenyl)-5-guanidinoimino-4-trifluoromethyl-5,6,7,8-tetrahydrocinnoline methanesulfonate (Compound 136) (0.240 g) as yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 80 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added sodium hydrogen carbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in acetone
  8. additionto the solution was added methanesulfonic acid (0.15 ml)
  9. customPrecipitated crystals
  10. filtrationwere filtered
  11. washwashed with acetone
  12. customdried

Sources & evidence

ORD record
ord-627e9fa394df46b087910c1ed740cf0b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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