m-Chloroperbenzoic acid → 4-Allyloxy-8-(2-benzimidazolyl)sulfinyl-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 649180Notes

Reaction equation

[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([S:15][C:16]3[NH:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:25])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([S:15]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=3)=[O:34])[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:25])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 60 °C

Procedure

0.7 Gram of 4-allyloxy-8-(2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline was dissolved in 30 ml of methylene chloride, then this solution was cooled to -50° to 31 60° C., next to this solution was added dropwise a solution prepared by dissolving 0.43 g of 80%-meta-chloroperbenzoic acid in 10 ml of methylene chloride, and the reaction mixture was stirred for 20 minutes at the above-mentioned temperature. After the reaction was completed, the reaction mixture was washed with an aqueous solution of sodium carbonate, and dried with anhydrous magnesium sulfate. Methylene chloride was removed by evaporation under reduced pressure, the residue thus obtained was recrystallized from diethyl ether to obtain 0.4 g of 4-allyloxy-8-(2-benzimidazolyl)sulfinyl-3-methyl-5,6,7,8-tetrahydroquinoline. White powdery crystals. Melting point: 100°-102° C. (decomposed)

Workup

additionwas added dropwise a solution
customprepared
washthe reaction mixture was washed with an aqueous solution of sodium carbonate
dry with materialdried with anhydrous magnesium sulfate
customMethylene chloride was removed by evaporation under reduced pressure
customthe residue thus obtained
customwas recrystallized from diethyl ether

Sources & evidence

ORD record: ord-8ec0bea902874e83aa9684ecc92b7c76
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738970

Reaction notes

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