4-Amino-1-butanol → 4-(1,2-Benzisoxazol-3-ylamino)-1-butanol

HRID 275744노트

반응식

HRID 275744 반응식
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(Cl)Cl.[I-].[K+]>[O:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[N:3]1

참가 물질

5

반응물 2

HCID 258684-Amino-1-butanolHCID 27797803-Chloro-1,2-benzoxazole

생성물 1

HCID 183789574-(1,2-Benzisoxazol-3-ylamino)-1-butanol수율 93.3%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-chloro-1,2-benzisoxazole (0.08 mol), 4-amino-1-butanol (0.24 mol) and potassium iodide (1 g) was stirred for 4 days at 80° C. The reaction mixture was cooled, dissolved in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 15.4 g (93%)of 4-(1,2-benzisoxazol-3-ylamino)-1-butanol (interm. 7). b) SOCl2 (0.048 mol) was cooled to 0° C. A solution of intermediate 7 (0.048 mol) in CHCl3 (20 ml) was added dropwise and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated. The residue was washed with water. The reaction mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent was evaporated, yielding 10.4 g of N-(4-chlorobutyl)-1,2-benzisoxazol-3-amine (interm. 8).

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompurified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-a37a3a890d5242feba69af330434052b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352999B1

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