Formaldehyde → 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

HRID 1782188ノート

反応式

HRID 1782188 の反応式
[H-].[Na+].[H][H].Cl.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][N:20]=2)[O:16][N:15]=1.[CH2:26]=O.[CH:28]([OH:31])([CH3:30])[CH3:29]>O>[Cl:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=1[C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([NH:25][CH2:26][O:31][CH:28]([CH3:30])[CH3:29])[CH:22]=[CH:21][N:20]=2)[O:16][N:15]=1

参加物

7

反応物 5

HCID 712FormaldehydeHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 69053436HCID 69053436、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 575884942-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Sodium hydride (120 mg, 2.9 mmol) was added slowly to isopropyl alcohol (15 mL) at 0° C. Once the evolution of hydrogen ceased 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine hydrochloride (200 mg, 0.58 mmol) and paraformaldehyde (147 mg, 1.64 mmol) added. The resulting mixture was stirred at room temperature for 5 h and hydrolyzed with ice-cooled water and extracted with ethyl acetate. The organic extracts were washed with water, then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine (269 mg). The product was carried forward without further purification. 1H NMR (CDCl3): 8.38 (d, 1H), 7.44 (m, 1H), 7.35 (m, 1H), 7.00 (s, 1H), 6.70 (m, 1H), 4.80 (d, 2H), 3.90 (m, 1H), 1.22 ppm (d, 6H).

後処理

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-67ba2c47208b41cfba83c3a8e0553269
出典データセット
uspto-grants-2009_03
特許番号
US07498353B2

反応ノート

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