Diisopropylamine → 1H-Pyrazole-4-carboxylic acid, 3-(4-chlorophenyl)-1-(((4-chlorophenyl)amino)carbonyl)-4,5-dihydro-4-methyl-, methyl ester

HRID 1607221노트

반응식

HRID 1607221 반응식
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[CH2:27][CH:26]([CH3:28])[C:25]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[N:24]2)=[O:22])=[CH:16][CH:15]=1.[CH3:36][O:37][C:38](=O)[O:39]C>O1CCCC1.CCCCCC.C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]2[CH2:27][C:26]([C:38]([O:37][CH3:36])=[O:39])([CH3:28])[C:25]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)=[N:24]2)=[O:22])=[CH:18][CH:19]=1

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 12021Dimethyl CarbonateHCID 13752557N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 1758551H-Pyrazole-4-carboxylic acid, 3-(4-chlorophenyl)-1-(((4-chlorophenyl)amino)carbonyl)-4,5-dihydro-4-methyl-, methyl ester

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To 3.1 g of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice salt bath was added 8.0 ml of a 2.7 molar solution of n-butyllithium in hexane. After stirring for 5 minutes a solution of 3.4 g of N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 7 ml of tetrahydrofuran was added and the resulting solution stirred for 15 minutes. To this solution was added 1.5 ml of dimethylcarbonate and, after 15 minutes 1.5 ml of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered and evaporated in vacuo to give 3.0 g of N,3-bis-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, mp 122° C. NMR and IR data were consistent with the structure.

후처리

  1. temperaturecooled in an ice salt bath
  2. additionwas added
  3. customThe reaction mixture was partitioned between diethyl ether and water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe resulting solution was filtered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-99ec301729b04b63837ba7e68eac57bb
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863947

반응 노트

불러오는 중…