Dimethyl Sulfide → Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

HRID 583693노트

반응식

HRID 583693 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][C:8]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=O.CSC>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][CH2:8][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 1068Dimethyl SulfideHCID 18928580Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

생성물 1

HCID 18928557Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Amide 24-3 (1.0 g, 3.4 mmol) was dissolved in 7 mL toluene at 0°, and BH3.DMS (341 μL, 3.6 mmol) was added. After 15 min, the reaction was heated to reflux for 16 h, cooled to 0°, and quenched with 10% Na2CO3. The mixture was extracted with EtOAc, the organic phase was washed with water and brine, dried (MgSO4), concentrated, and purified by flash chromatography (silica, 70% EtOAc/hexane) providing 24-4 as a white solid. Rf 0.64 (silica, EtOAc).

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 h
  3. temperaturecooled to 0°
  4. customquenched with 10% Na2CO3
  5. extractionThe mixture was extracted with EtOAc
  6. washthe organic phase was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (silica, 70% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-23d2597344324be4a5ccd85f6bff66d1
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929120

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