Hydrogen Sulfide → 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester

HRID 47288

반응식

HRID 47288 반응식
[SH2:1].[CH2:2]([S:4][C:5](=N)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][CH2:14][C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[CH3:3].Cl.CCOCC>O1CCCC1.O>[CH2:2]([S:4][C:5](=[S:1])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][CH2:14][C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[CH3:3]

참가 물질

6

반응물 3

HCID 402Hydrogen SulfideHCID 10953452Ether hydrochlorideHCID 206283952-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-thiobenzimidic acid ethyl ester

생성물 1

HCID 206283942-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

As shown in Scheme 11, hydrogen sulfide gas (˜2 mL) was condensed into a cooled (−78° C.) solution of 2.8 grams (6.8 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-thiobenzimidic acid ethyl ester and 13.6 mL (13.6 mmol) of 1.0 M HCl/ether in 100 mL of tetrahydrofuran. The reaction was heated to 45° C. and stirred overnight in a sealed tube. The reaction mixture was diluted with water and extracted with methylene chloride once. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to give a crude orange oil. The oil was partially purified by chromatography through a short column of silica gel (eluting with 5:95 ethyl acetate/hexanes) which resulted in 1.8 g of an orange powder which was used directly in the next step.

후처리

  1. customcondensed into
  2. extractionextracted with methylene chloride once
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude orange oil
  8. customThe oil was partially purified by chromatography through a short column of silica gel (eluting with 5:95 ethyl acetate/hexanes) which

출처 및 근거

ORD 기록
ord-3d91358cdd8a44388a63432ff509d171
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699873B1

연결된 노트

불러오는 중…