Tert-Butanesulfinamide → 2-Methyl-propane-2-sulfinic acid 1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylideneamide

HRID 578855노트

반응식

HRID 578855 반응식
[Cl:1][C:2]1[C:3]([C:12]2([CH:15]=O)[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:17][C:18]([S:21]([NH2:23])=[O:22])([CH3:20])[CH3:19]>O1CCCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][C:2]1[C:3]([C:12]2([CH:15]=[N:23][S:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

참가 물질

6

반응물 2

HCID 3382465Tert-ButanesulfinamideHCID 715592821-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropanecarbaldehyde

생성물 1

HCID 781117472-Methyl-propane-2-sulfinic acid 1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylideneamide수율 71.7%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

0.72 g of 1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropanecarbaldehyde (step 2) was dissolved in 13 ml of tetrahydrofuran, then 1.32 g of titanium(IV)ethoxide and 355 mg of 2-methyl-propane-2-sulfinic acid amide were added to the solution. The reaction mixture was stirred at ambient temperature for 24 hours, then poured into brine. The resulting suspension was filtered, the filtrate extracted with ethyl acetate, the organic phase dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (95:5) as eluent. Thus, 0.73 g of 2-methyl-propane-2-sulfinic acid 1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylideneamide was obtained as a pale yellow solid. 1H-NMR (CDCl3): 8.73 ppm (s, 1H), 7.95 ppm (s, 1H), 7.65 ppm (s, 1H), 1.70 ppm (m, 4H), 1.12 ppm (s, 9H).

후처리

  1. filtrationThe resulting suspension was filtered
  2. extractionthe filtrate extracted with ethyl acetate
  3. dry with materialthe organic phase dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with cyclohexane/ethyl acetate (95:5) as eluent

출처 및 근거

ORD 기록
ord-44b64083462b432cb8e44718c7dc5f8f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040708B2

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