Dichloromethane → HCID 22646606, compound

HRID 393681Notes

Reaction equation

HRID 393681 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:22][CH3:23])=[C:14]([S:17][CH2:18][CH2:19][O:20][CH3:21])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:26])[CH:3]=1.[OH:27]OS([O-])=O.[K+].C(Cl)Cl.C(OCC)(=O)C.CO>CO.O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:22][CH3:23])=[C:14]([S:17]([CH2:18][CH2:19][O:20][CH3:21])=[O:27])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:26])[CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 21584119Ethylacetate methanolHCID 22646598HCID 22646598, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 22646606HCID 22646606, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(4-Chloro-2-fluoroanilino)-7-methoxy-6-(2-methoxyethylthio)quinoline (175 mg, 0.45 mmol), (prepared as described in Example 62), was dissolved in methanol (40 ml), OXONE, (trade mark of E.I. du Pont de Nemours & Co.,Inc), (230 mg in 5 ml of water) was added and the mixture was stirred at ambient temperature for 30 minutes. More OXONE, (trade mark of E.I. du Pont de Nemours & Co.,Inc), (60 mg) was added and the mixture was stirred for a further hour. The mixture was diluted with 100 ml of water and extracted with methylene chloride (3×100 ml). The combined extracts were washed with brine, dried by passing through phase separating paper and the volatiles were removed by evaporation. The solid was purified on a Mega Bond Elute (trade mark of Varian Sample Preparation Products) column using first methylene chloride (100%) and gradually increasing the solvent polarity up to methylene chloride/methanol (95/5). The volatiles were removed by evaporation to give 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-(2-methoxyethylsulphinyl)quinoline (120 mg, 66%).

Workup

  1. stirringthe mixture was stirred for a further hour
  2. extractionextracted with methylene chloride (3×100 ml)
  3. washThe combined extracts were washed with brine
  4. customdried
  5. customseparating paper
  6. customthe volatiles were removed by evaporation
  7. customThe solid was purified on a Mega Bond
  8. washElute
  9. custom(trade mark of Varian Sample Preparation Products) column
  10. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-cce643d053b34787a1406524fbaeaf4f
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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