Ethanol → Ethyl 4-(trifluoromethyl)thiazole-2-carboxylate

HRID 388702노트

반응식

HRID 388702 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8]([OH:10])=[O:9])[S:6][CH:7]=1.O=S(Cl)Cl.[CH3:17][CH2:18]O>>[CH2:17]([O:9][C:8]([C:5]1[S:6][CH:7]=[C:3]([C:2]([F:1])([F:11])[F:12])[N:4]=1)=[O:10])[CH3:18]

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 186730104-(Trifluoromethyl)thiazole-2-carboxylic acid

생성물 1

HCID 23560697Ethyl 4-(trifluoromethyl)thiazole-2-carboxylate수율 96%

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온도
40 °C

실험 절차

To a stirred solution of 4-trifluoromethylthiazole-2-carboxylic acid (98 g, 1 eq.) in EtOH (600 mL) was added dropwise SOCl2 (36 mL, 1 eq.). The mixture was stirred at 40° C. for 8 hrs and then at room temperature for 16 hrs. The reaction mixture was concentrated under reduced pressure and the residue was redissolved in DCM. Organics were washed with saturated aqueous NaHCO3 solution, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 281 as a brown solid in 96% yield. 1H NMR (CDCl3, 400 MHz) δ 1.45 (t, J=7.14 Hz, 3H), 4.49-4.54 (q, J=7.10 Hz, 2H), 8.02 (s, 1H).

후처리

  1. waitat room temperature for 16 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was redissolved in DCM
  4. washOrganics were washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bbddfdda21b3474e8762a96f55e7595d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377962B2

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