Dichloromethane → Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

HRID 879345노트

반응식

HRID 879345 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.Br[C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1.C(Cl)[Cl:50]>>[Cl:50][C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 159087Triacetoxyperiodinane2회HCID 86699782Ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

생성물 1

HCID 86700145Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

반응 조건

온도
0 °C

실험 절차

The above residue was dissolved in CH2Cl2 (33 mL), cooled to 0° C. and Dess-Martin periodinane (2.54 g, 5.99 mmol) was added portion-wise. After stirring for 2 h, more Dess-Martin periodinane (0.25 g, 5.99 mmol) was added. After 1 h, reaction was quenched with Na2S2O3 solution and stirred for 30 minutes. The mixture was diluted with CH2Cl2, washed with water, saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 20% EtOAc/Hex) to give product contaminated with ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate 1H NMR (400 MHz, CDCl3): δ 7.88 (s, 1H), 4.42 (q, J=7.2 Hz, 2H), 2.49 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).

후처리

  1. waitAfter 1 h
  2. customreaction
  3. customwas quenched with Na2S2O3 solution
  4. stirringstirred for 30 minutes
  5. additionThe mixture was diluted with CH2Cl2
  6. washwashed with water, saturated sodium bicarbonate solution, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by CombiFlash (0 to 20% EtOAc/Hex)
  11. customto give product

출처 및 근거

ORD 기록
ord-ec671ea85364413588080f6691373f54
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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