Carbon Disulfide → 2-((Butylsulfanyl)carbonothioyl)sulfanyl)propanoic acid

HRID 20184

반응식

HRID 20184 반응식
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4]CCCCCCCC.[OH-].[Na+].[C:16](=[S:18])=[S:17].Br[CH:20]([CH3:24])[C:21]([OH:23])=[O:22]>[Br-].C([N+](CCC)(CCC)CCC)CC.O.CC(C)=O>[CH2:1]([S:13][C:16]([S:18][CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[S:17])[CH2:2][CH2:3][CH3:4]

참가 물질

8

반응물 4

HCID 6348Carbon DisulfideHCID 81951-DodecanethiolHCID 117292-Bromopropionic acidHCID 14798Sodium Hydroxide

생성물 1

HCID 593471542-((Butylsulfanyl)carbonothioyl)sulfanyl)propanoic acid수율 111.7%

시약·촉매·용매 3

HCID 74745Tetrapropylammonium bromide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

Dodecanethiol (2.50 g, 12.5 mmol), acetone (40 mL), and tetrapropylammonium bromide (0.27 g, 0.10 mmol) were added to a solution of sodium hydroxide (0.50 g, 12.5 mmol) in water (5 mL). The resulting solution was cooled in an ice bath and treated with carbon disulfide (0.75 mL, 0.95 g, 12.5 mmol). After 20 min, 2-bromopropanoic acid (1.91 g, 12.5 mmol) was added and the mixture was stirred at ambient temperature for 12 h. The solution was evaporated to ¼ volume and slowly acidified with 2 M hydrochloric acid (50 mL), then further diluted with water (150 mL). The resulting solid was collected and recrystallised from ether/light petroleum to give the title compound (15, R3=C12H25) as yellow crystals (3.33 g, 76%).

후처리

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customThe solution was evaporated
  3. additionfurther diluted with water (150 mL)
  4. customThe resulting solid was collected
  5. customrecrystallised from ether/light petroleum

출처 및 근거

ORD 기록
ord-cbdd9b4994364bda8b1573b9e3f599bd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745553B2

연결된 노트

불러오는 중…