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

HRID 1892539노트

반응식

HRID 1892539 반응식
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

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2723593Acetylthiourea2회HCID 86227322N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}thiazol-2-yl)acetamide

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6b5dc05936ed4c9bab2805d7f41537d1
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507690B2

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