Triethylamine → HCID 76759590, 화합물

HRID 444704노트

반응식

HRID 444704 반응식
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8](=O)[CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O=P(Cl)(Cl)[Cl:20].CCN(CC)CC>C(Cl)(Cl)Cl>[Cl:20][C:8]([C:3]1[S:4][CH:5]=[C:6]([CH3:7])[C:2]=1[Cl:1])=[C:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 67115664HCID 67115664, 화합물

생성물 1

HCID 76759590HCID 76759590, 화합물수율 66.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
5 °C

실험 절차

To a solution of ethyl 3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-oxopropanoate (15.40 g, 56.67 mmol, 1 eq.) in 200 ml of CHCl3 was added POCl3 (86.9 g, 566 mmol, 10 eq.). Et3N (14.33 g, 141.6 mmol, 2.5 eq.) was added dropwise with stirring at 5° C., and the mixture was refluxed for 4 h. The mixture was evaporated. After evaporation, the mixture was diluted with DCM (CH2Cl2) and with ice water and was extracted with DCM (CH2Cl2) and washed with brine. The organic layers were combined and dried over MgSO4 before concentration under reduced pressure. The residue was subjected to column chromatography on silica gel to give ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (11 g, 66% yield) as a mixture of 2 isomers

후처리

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe mixture was evaporated
  3. customAfter evaporation
  4. additionthe mixture was diluted with DCM (CH2Cl2) and with ice water
  5. extractionwas extracted with DCM (CH2Cl2)
  6. washwashed with brine
  7. dry with materialdried over MgSO4 before concentration under reduced pressure

출처 및 근거

ORD 기록
ord-4847b81d5f864422aa202a73eb9b298b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476197B2

반응 노트

불러오는 중…