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

HRID 1782188노트

반응식

HRID 1782188 반응식
[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

참가 물질

7

반응물 5

HCID 712FormaldehydeHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 69053436HCID 69053436, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-67ba2c47208b41cfba83c3a8e0553269
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498353B2

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