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O-p-Chlorophenyl chlorothioformate → 5-{4-[(2-Methoxy-ethyl)-methyl-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester

HRID 2212535
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인쇄 미리보기

반응식

HRID 2212535 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29](Cl)=[S:30])=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O.CCOCC>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[S:30])=[CH:24][CH:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 70306O-p-Chlorophenyl chlorothioformateHCID 516892Sodium BicarbonateHCID 21966650[4-(2,3-Dihydro-1H-indol-5-yloxy)-butyl]-(2-methoxy-ethyl)-methyl-amine

생성물 1

HCID 865870115-{4-[(2-Methoxy-ethyl)-methyl-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester수율 64%

시약·촉매·용매 3

HCID 962Water
용매
HCID 3283Diethyl Ether용매
HCID 312751,4-Dioxane용매2회

실험 절차

220 mg (0.8 mmol) [4-(2,3-Dihydro-1H-indol-5-yloxy)-butyl]-(2-methoxy-ethyl)-methyl-amine in 0.5 ml dioxane were treated with 186 mg (0.9 mmol) chloro-thioformic acid (4-chloro-phenyl)ester in 0.5 ml dioxane at 0° C. The solution was stirred at RT for 3 h, was diluted with water and ether and a saturated aqueous solution of NaHCO3 was added. The inorganic layer was extracted with ether, washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 230 mg (64%) 5-{4-[(2-Methoxy-ethyl)-methyl-amino]-butoxy}-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester as yellow viscous oil, MS: 449 (MH+, 1Cl).

후처리

  1. extractionThe inorganic layer was extracted with ether
  2. washwashed with water
  3. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-6c2f6ddfe8034443be74bdd41f44ace6
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07102007B2

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