Toluene → Diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-1-(2-[N,N-bis-(methoxyethyl)]aminoethyl)-3,5-pyridine dicarboxylate

HRID 463533

반응식

HRID 463533 반응식
[H-].[Na+].[F:3][C:4]([F:30])([F:29])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[NH:14][C:13]([CH3:23])=[C:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].C1(C)C=CC=CC=1.Cl[CH2:39][CH2:40][N:41]([CH2:46][CH2:47][O:48][CH3:49])[CH2:42][CH2:43][O:44][CH3:45]>CN(C=O)C>[F:30][C:4]([F:29])([F:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:13]([CH3:23])[N:14]([CH2:39][CH2:40][N:41]([CH2:46][CH2:47][O:48][CH3:49])[CH2:42][CH2:43][O:44][CH3:45])[C:15]([CH3:22])=[C:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 1680891,4-Dihydro-2,6-dimethyl-4-(2-(trifluoromethyl)phenyl)-3,5-pyridinedicarboxylic acid diethyl esterHCID 156595712-chloro-N,N-bis(methoxyethyl)ethylamine

생성물 1

HCID 20281063Diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-1-(2-[N,N-bis-(methoxyethyl)]aminoethyl)-3,5-pyridine dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a suspension of sodium hydride (5.2 gms.; 0.11 mole) (50% suspension mineral oil) in 100 ml of dry distilled DMF is added a solution of diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate (39.7 gms.; 0.1 mole) in 150 ml of DMF. After the gassing has ceased, the reaction mixture is heated on a water bath for 1 hour and then is cooled to 50° C. and to the hot solution is added a toluene solution of 2-chloro-N,N-bis(methoxyethyl)ethylamine. The reaction mixture is heated at 100°-110° C. for a period of 8 hours and then cooled. The unreacted NaH and NaCl is filtered off and the solvent removed from the filtrate. The residue is extracted with hot hexane which, on cooling, affords the desired product. Recrystallization from heptane yields the pure product.

후처리

  1. customof dry
  2. distillationdistilled DMF
  3. temperaturethe reaction mixture is heated on a water bath for 1 hour
  4. temperatureThe reaction mixture is heated at 100°-110° C. for a period of 8 hours
  5. temperaturecooled
  6. filtrationThe unreacted NaH and NaCl is filtered off
  7. customthe solvent removed from the filtrate
  8. extractionThe residue is extracted with hot hexane which
  9. temperatureon cooling

출처 및 근거

ORD 기록
ord-19e44a28db16498895aff6545ae620b0
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04520131

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