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

HRID 2380500Notes

Reaction equation

HRID 2380500 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f5b163ebf7eb42c0899231ac4b06461f
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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