Chlorosuccinimide → Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate

HRID 385401ノート

反応式

HRID 385401 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1.C1C(=O)N([Cl:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.O>[NH2:1][C:2]1[C:3]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][C:7]=1[Cl:26]

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 57995628Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate

生成物 1

HCID 57995503Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate収率 101.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a stirred solution of ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate (1.2 g, 4.0 mmol) in dry CCl4 (60 mL), NCS (0.427 g, 3.2 mmol) was added at 0° C. The reaction mixture was allowed to stir for 3 h at room temperature. The reaction mixture was diluted with water and extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and the volatiles removed in vacuo. The crude reaction mixture was purified by column chromatography to give ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate (920 mg) as a yellow solid.

後処理

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe volatiles removed in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-6853de6e47a8410b83b2981282cf9b22
出典データセット
uspto-grants-2013_02
特許番号
US08367863B2

反応ノート

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