Benzene → HCID 178513132, compound

HRID 1700675Notes

Reaction equation

HRID 1700675 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:22])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[N:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[C:10]=2[C:9](=O)[CH2:8]1.[C:23]([NH:26][NH2:27])([NH2:25])=[NH:24].Cl.CS(O)(=O)=O.C1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[S:3][C:4]([Cl:22])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[N:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[C:10]=2[C:9](=[N:27][NH:26][C:23]([NH2:25])=[NH:24])[CH2:8]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6395Methanesulfonic AcidHCID 183174187-(2,5-Dichlorothiophen-3-yl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-oneHCID 178418668HCID 178418668, compound

Product 1

HCID 178513132HCID 178513132, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(2,5-dichlorothiophen-3-yl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-one (0.443 g) and aminoguanidine hydrochloride (167 mg) in ethanol (10 ml) were added methanesulfonic acid (0.2 ml) and benzene (10 ml), and the mixture was refluxed for 1.5 hours. 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 washed with isopropylether and diethylether and dried to give 7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-trifluoromethyl-5,6,7,8-tetrahydrocinnoline (Compound 135) (0.160 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  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. washThe residue was washed with isopropylether and diethylether
  8. customdried

Sources & evidence

ORD record
ord-4fb92a050679497984c9534849d5ad91
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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