Sodium borohydride → (3-(4-Chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methanol

HRID 453113노트

반응식

HRID 453113 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13](OCC)=[O:14])[S:10][N:9]=2)=[C:4]([O:18][CH3:19])[CH:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][OH:14])[S:10][N:9]=2)=[C:4]([O:18][CH3:19])[CH:3]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 59549519Ethyl 3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole-5-carboxylate

생성물 1

HCID 59549528(3-(4-Chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methanol수율 92%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of ethyl 3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole-5-carboxylate (0.31 g, 1.04 mmol) in EtOH (15 ml) was added sodium borohydride (0.098 g, 2.59 mmol) portion wise. The resulting reaction mixture was stirred at room temperature for 2 h. After the completion of the reaction (TLC monitoring), the reaction mass was cooled to 0° C., quenched it with 2 ml of water and concentrated under vacuum. Added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum to get the product (0.22 g, 92%) that was carried forward to the next step without further purification.

후처리

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mass was cooled to 0° C.
  4. customquenched it with 2 ml of water
  5. concentrationconcentrated under vacuum
  6. extractionAdded water (50 ml) and extracted with ethyl acetate (3×50 ml)
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-1f964dd4b88b4e8582cb768019234da5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492414B2

반응 노트

불러오는 중…