Formaldehyde → 3-{2-(1-Pyrrolidinylmethyl)-butyryl}-1,2-benzisoxazole

HRID 1742544

반응식

HRID 1742544 반응식
[C:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].C=O.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[C:22](=O)([O-])O.[Na+]>C(OCC)(=O)C.C(O)C>[N:17]1([CH2:22][CH:2]([CH2:3][CH3:4])[C:1]([C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][N:7]=2)=[O:5])[CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 199769213-Butyryl-1,2-benzisoxazole

생성물 1

HCID 199769433-{2-(1-Pyrrolidinylmethyl)-butyryl}-1,2-benzisoxazole

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

Added to 10 ml of ethanol were 1.55 g (8.2 mmol) of 3-butyryl-l,2-benzisoxazole prepared above in the procedure (1), 0.52 ml (9.9 mmol) of a 37% aqueous solution of formaldehyde and 0.82 ml (9.8 mmol) of pyrrolidine. The resultant mixture was heated under reflux for 3 hours. After cooling, the solvent was distilled off. The residue thus obtained was added to 50 ml of ethyl acetate, followed by extraction with 50 ml of dilute hydrochloric acid. A water layer thus obtained was alkalinized with an aqueous solution of sodium hydrogencarbonate, followed by extraction with 50 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then distilled off, whereby 3-{2-(1-pyrrolidinylmethyl)-butyryl}-1,2-benzisoxazole was obtained as oil. Analytical results of the crystals obtained: Yield: 1.65 g (74%).

후처리

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customThe residue thus obtained
  5. extractionfollowed by extraction with 50 ml of dilute hydrochloric acid
  6. customA water layer thus obtained
  7. extractionfollowed by extraction with 50 ml of ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was then distilled off

출처 및 근거

ORD 기록
ord-cb88790a5c97476f9270e5e053e4b318
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338857

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