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

HRID 264094ノート

反応式

HRID 264094 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7845cfd4d872454cb811373df0b130ee
出典データセット
uspto-grants-1997_07
特許番号
US05646170

反応ノート

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