Carbon Disulfide → 3-{[(tert-butylsulfanyl)carbonothioyl]sulfanyl}propanoic Acid

HRID 20186

반응식

HRID 20186 반응식
[OH-].[Na+].[C:3]([SH:7])([CH3:6])([CH3:5])[CH3:4].[C:8](=[S:10])=[S:9].Br[CH:12]([CH3:16])[C:13]([OH:15])=[O:14]>O.[Br-].C([N+](CCC)(CCC)CCC)CC.CC(C)=O>[C:3]([S:7][C:8]([S:10][CH2:16][CH2:12][C:13]([OH:15])=[O:14])=[S:9])([CH3:6])([CH3:5])[CH3:4]

참가 물질

8

반응물 4

HCID 6348Carbon DisulfideHCID 6387tert-Butyl mercaptanHCID 117292-Bromopropionic acidHCID 14798Sodium Hydroxide

생성물 1

HCID 593471453-{[(tert-butylsulfanyl)carbonothioyl]sulfanyl}propanoic Acid

시약·촉매·용매 3

HCID 74745Tetrapropylammonium bromide촉매HCID 180Acetone용매HCID 962Water용매2회

실험 절차

A solution of sodium hydroxide (1.0 g; 25 mmol) in water (5 mL) was added to acetone (70 mL) followed by tetrapropylammonium bromide (0.53 g; 20 mmol) and then tert-butyl mercaptan (2.26 g; 25 mmol; 2.82 mL) with stirring forming a white precipitate. After 20 min. carbon disulfide (2.12 g; 27.5 mmol; 1.67 mL) was added dropwise causing the precipitate to slowly disappear and an orange solution to form. After stirring the resulting solution for an additional 40 min, 2-bromopropanoic acid (3.83 g; 25 mmol; 2.26 mL) was added dropwise and then the whole was stirred for 18 h. Acetone and excess carbon disulfide were removed under high vacuum to give an orange oil. This was diluted with water (100 mL) giving an aqueous solution of pH 4. This was extracted with ether, the combined extracts were dried (Na2SO4) and the solvent was removed under high vacuum. The remaining viscous orange oil was frozen in liquid nitrogen and kept in the freezer for 20 h during which time a solid mass developed. The solid was triturated with hexane with stirring for 2 h and then filtered, washing with more hexane. The title compound was obtained as a yellow solid (2.06 g; 35%).

후처리

  1. customforming a white precipitate
  2. customan orange solution to form
  3. stirringthe whole was stirred for 18 h
  4. customAcetone and excess carbon disulfide were removed under high vacuum
  5. customto give an orange oil
  6. customgiving an aqueous solution of pH 4
  7. extractionThis was extracted with ether
  8. dry with materialthe combined extracts were dried (Na2SO4)
  9. customthe solvent was removed under high vacuum
  10. temperatureThe remaining viscous orange oil was frozen in liquid nitrogen
  11. waitkept in the freezer for 20 h during which time
  12. customThe solid was triturated with hexane
  13. stirringwith stirring for 2 h
  14. filtrationfiltered
  15. washwashing with more hexane

출처 및 근거

ORD 기록
ord-3d021d1020c5471b90caccd14801eb21
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745553B2

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