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

HRID 978168ノート

反応式

HRID 978168 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:15][CH:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:12]2)=[O:10])=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C([Li])CCC.Cl[C:37]([O:39][CH3:40])=[O:38]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]2[CH2:15][C:14]([C:37]([O:39][CH3:40])=[O:38])([CH3:16])[C:13]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[N:12]2)=[O:10])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 7912DiisopropylamineHCID 13752557N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

To 3.4 g of N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide and 1.1 g of diisopropylamine dissolved in 20 ml of tetrahydrofuran and cooled in an acetone bath maintained at -20° C., was added 8.0 ml of a 2.7 molar solution of butyllithium in hexane. The resulting solution was stirred for 20 minutes and then cooled to -70° C. To this solution was added 0.9 ml of methyl chloroformate. The reaction was allowed to stir for 10 minutes and then allowed to warm to room temperature over 10 minutes. The reaction was quenched with 1.0 ml of acetic acid and 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 evaporated in vacuo to give 2.9 g of N,3-bis-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. NMR and IR data were consistent with the structure.

後処理

  1. temperaturecooled in an acetone bath
  2. temperaturecooled to -70° C
  3. stirringto stir for 10 minutes
  4. temperatureto warm to room temperature over 10 minutes
  5. customThe reaction was quenched with 1.0 ml of acetic acid
  6. customthe reaction mixture was partitioned between diethyl ether and water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationThe resulting solution was filtered
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-dc2c67269bc2469683eaa28f3a594278
出典データセット
uspto-grants-1987_05
特許番号
US04663341

反応ノート

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