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Bromoacetic Acid → [{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acid

HRID 486903
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HRID 486903 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Br[CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>C(O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

생성물 1

HCID 19001624[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acid수율 93.2%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water
용매

실험 절차

100 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 75.1 g of bromoacetic acid were dissolved in 1 l of ethanol. A solution of 44 g of sodium hydroxide in 125 ml of water and then 2 l of ethanol were added thereto. The mixture was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure. 2.5 l of water was added thereto. The mixture was made alkaline with a 1N sodium hydroxide solution, washed with 35% hydrochloric acid, extracted with ethyl acetate, washed with water four times and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 121 g of [{2-(1,3-benzodioxol-5-yl)ethyl}thio]acetic acid in the form of a faint yellow oil.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. addition2.5 l of water was added
  5. washwashed with 35% hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washwashed with water four times
  8. dry with materialdried over sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-0c0e27bcb8b04d4695aa445e55300cd2
출처 데이터셋
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05292901

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