Triethylamine → (+/-)-4-(1-Dodecenyl)-alpha-phenyl-N-(2,4,6-trimethoxyphenyl)-1H-pyrazole-1-acetamide

HRID 264094노트

반응식

HRID 264094 반응식
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[C:12]=1[NH2:13].[CH:22]([C:34]1[CH:35]=[N:36][N:37]([CH:39]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:40](O)=[O:41])[CH:38]=1)=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.ClCCl>[CH:22]([C:34]1[CH:35]=[N:36][N:37]([CH:39]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:40]([NH:13][C:12]2[C:14]([O:20][CH3:21])=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[O:10][CH3:9])=[O:41])[CH:38]=1)=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27644342,4,6-trimethoxyaniline HydrochlorideHCID 53719716(+/-)-4-(1-Dodecenyl)-alpha-phenyl-1H-pyrazole-1-acetic acid

생성물 1

HCID 53740607(+/-)-4-(1-Dodecenyl)-alpha-phenyl-N-(2,4,6-trimethoxyphenyl)-1H-pyrazole-1-acetamide수율 72.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (18 mL, 130 mmol) was added to a suspension of 2,4,6-trimethoxyaniline hydrochloride (28.48 g, 130 mmol) in 500 mL THF and stirred for 1 hour before filtering to remove triethylamine hydrochloride. The filtrate was concentrated and redissolved in 500 mL dichloromethane along with (±)-4-(1-dodecenyl)-α-phenyl-1H-pyrazole-1-acetic acid (43.43 g, 118 mmol) at -15° C. Dicyclohexylcarbodiimide (25.53 g, 124 mmol) was added in one portion and the resulting suspension was warmed to room temperature and stirred for 16 hours. Filtered to remove a white solid and partitioned the filtrate between dichloromethane and 1N HCl. The organic layer was dried over MgSO4, filtered, and concentrated to give an oily tan solid. Recrystallized from hexanes to give the title compound as a tan solid (45.43 g, 72%); mp 82°-85° C.

후처리

  1. filtrationbefore filtering
  2. customto remove triethylamine hydrochloride
  3. concentrationThe filtrate was concentrated
  4. stirringstirred for 16 hours
  5. filtrationFiltered
  6. customto remove a white solid
  7. custompartitioned the filtrate between dichloromethane and 1N HCl
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oily tan solid
  12. customRecrystallized from hexanes

출처 및 근거

ORD 기록
ord-7845cfd4d872454cb811373df0b130ee
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646170

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