Ethyl Acetate → N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

HRID 1892539ノート

反応式

HRID 1892539 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.C(NC(N)=[S:26])(=O)C.C(OCC)(=O)C>C(O)C>[SH:26][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2723593Acetylthiourea2 回HCID 86227322N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}thiazol-2-yl)acetamide

生成物 1

HCID 86650044N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide収率 68.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (353.3 mg, 1.000 mmol) in ethanol (4 ml) was added 1-acetyl-2-thiourea (177.4 mg, 1.501 mmol), and the mixture was heated under reflux for 7 hr. 1-Acetyl-2-thiourea (176.6 mg, 1.495 mmol) was added, and the mixture was heated under reflux for 17 hr. The mixture was cooled to room temperature, ethyl acetate (10 ml) was added, and the precipitated solid was filtered off. The filtrate was concentrated under reduced pressure, and purified twice by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM-2035 21 g, ethyl acetate:hexane=2:3→1:1) to give N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (210.4 mg, 0.687 mmol, 68.7%) as a white solid.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 17 hr
  5. filtrationthe precipitated solid was filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified twice by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM-2035 21 g, ethyl acetate:hexane=2:3→1:1)

出典と根拠

ORDレコード
ord-6b5dc05936ed4c9bab2805d7f41537d1
出典データセット
uspto-grants-2013_08
特許番号
US08507690B2

反応ノート

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