m-Chloroperbenzoic acid → HCID 15053319, compound

HRID 1088816Notes

Reaction equation

HRID 1088816 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][S:13][C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:5]([CH3:23])=[CH:4][CH2:3]1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][S:13]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)=[O:32])[C:5]([CH3:23])=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22161795HCID 22161795, compound

Product 1

HCID 15053319HCID 15053319, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-Dimethyl-8-(2-benzimidazolyl)thiomethyl-1,2-dihydroquinoline (0.4 g) was dissolved in dichloromethane (30 ml). To this solution was added dropwise a solution of m-chloroperbenzoic acid (0.27 g) in dichloromethane (5 ml) at -40° C. with stirring. After the mixture was stirred for 20 minutes at the same temperature, the reaction mixture was washed with an aqueous solution of sodium carbonate and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. Diethyl ether was added to the resulting residue to precipitate crystals. The resulting crystals were recrystallized from dichloromethane-diethyl ether to give 1,4-dimethyl-8-(2-benzimidazolyl)sulfinylmethyl-1,2-dihydroquinoline (0.2 g).

Workup

  1. stirringAfter the mixture was stirred for 20 minutes at the same temperature
  2. washthe reaction mixture was washed with an aqueous solution of sodium carbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. additionDiethyl ether was added to the resulting residue
  7. customto precipitate crystals
  8. customThe resulting crystals were recrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-0d79c2bc826448f5bdc52128326fcb6a
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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