Triethylamine → 2-(4-Dodecyl-imidazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 2380505노트

반응식

HRID 2380505 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].[CH2:22]([C:34]1[N:35]=[CH: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)[CH2:23][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>[CH2:22]([C:34]1[N:35]=[CH: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)[CH2:23][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 10642923(+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acid

생성물 1

HCID 106976122-(4-Dodecyl-imidazol-1-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide수율 35.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Excess triethylamine (2 mL) was added to a suspension of 2,4,6-trimethoxyaniline hydrochloride (1.6 g, 7.3 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-dodecyl-α-phenyl-1H-imidazole-1-acetic acid (2.45 g, 6.6 mmol) at 0° C. Dicyclohexylcarbodiimide (1.43 g, 6.9 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 IN HCl. The organic layer was washed with 1N NaOH, dried over MgSO4, filtered, and concentrated. The resulting residue was chromatographed (20% EtOAc/hexanes on silica) to give the title compound as a white solid (1.25 g, 35%); mp 95°-102° 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
  8. washThe organic layer was washed with 1N NaOH
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe resulting residue was chromatographed (20% EtOAc/hexanes on silica)

출처 및 근거

ORD 기록
ord-6b1e36350dc5430cbdee3393faae3385
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05366987

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