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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
ノート
印刷プレビュー

反応式

HRID 2212535 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water
溶媒
HCID 3283Diethyl Ether溶媒
HCID 312751,4-Dioxane溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-6c2f6ddfe8034443be74bdd41f44ace6
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07102007B2

反応ノート

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