Sodium Carbonate → 8-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088815노트

반응식

HRID 1088815 반응식
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)[NH:9][C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)=[O:33])[NH:9][C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 150533118-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline수율 45.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.80 g) in dichloromethane (30 ml) was added a solution of m-chloroperbenzoic acid (80%, 0.51 g) in dichloromethane (10 ml) by use of a pipet at -60° C. The mixture was stirred for 30 minutes at the same temperature. Aqueous sodium carbonate was added to the reaction mixture and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)] and recrystallized from ethyl acetate to give 8-(5-methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.38 g).

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)]
  5. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-d9b986387d474111be66cccba7e251e4
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963566

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