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

HRID 578855ノート

反応式

HRID 578855 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-44b64083462b432cb8e44718c7dc5f8f
出典データセット
uspto-grants-2015_05
特許番号
US09040708B2

反応ノート

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