Triethylamine → N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide

HRID 2118985

반응식

HRID 2118985 반응식
[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:20][C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]=1[C:32](Cl)=[O:33]>O1CCCC1>[C:6]1([N:5]([CH2:4][CH2:3][N:2]([CH3:12])[CH3:1])[C:32]([C:22]2[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:24][O:25][C:21]=2[CH3:20])=[O:33])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 81206N-(2-(Dimethylamino)ethyl)anilineHCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chloride

생성물 1

HCID 13982559N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A mixture of 24.6 grams (0.15 mole) of N,N-dimethyl-N'-phenyl-ethylenediamine and 18.2 grams (0.18 mole) of triethylamine in 500 milliliters of tetrahydrofuran (THF) is cooled to 0° C. and 39.8 grams (0.18 mole) of 5-methyl-3-phenyl-4-isoxazole carbonyl chloride in 100 milliliters of tetrahydrofuran is added dropwise. After the addition is complete, the mixture is warmed to room temperature and stirred for 4 hours. The resulting suspension is filtered and the THF removed in vacuo. The residue is dissolved in methylene chloride and washed with 2N sodium hydroxide and water and then dried over magnesium sulfate. The mixture is filtered and the solvent removed by evaporation. The residue is then treated with hexane to yield crystals of N-phenyl-N-(2-dimethylaminoethyl)-5-methyl-3-phenyl-4-isoxazole carboxamide; M.P. 88°-89° C.

후처리

  1. additionAfter the addition
  2. temperaturethe mixture is warmed to room temperature
  3. filtrationThe resulting suspension is filtered
  4. customthe THF removed in vacuo
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with 2N sodium hydroxide and water
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe mixture is filtered
  9. customthe solvent removed by evaporation
  10. additionThe residue is then treated with hexane

출처 및 근거

ORD 기록
ord-bbbd39e7ea1b46b3b1dbc5fb251f40f1
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04681898

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