N-Methylbenzamide → HCID 21554039、化合物

HRID 267748

反応式

HRID 267748 の反応式
[CH3:1][NH:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][N:31]([CH3:33])[CH3:32])=[CH:19][CH:18]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][N:31]([CH3:33])[CH3:32])([OH:34])[C:5]2[C:4]([C:3]([NH:2][CH3:1])=[O:10])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 11954N-MethylbenzamideHCID 25517Ammonium ChlorideHCID 21554017(4-Chlorophenyl)[2-[(dimethylamino)methyl]phenyl]methanoneHCID 178418339Butyllithium

生成物 1

HCID 21554039HCID 21554039、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
5 °C

実験手順

To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 19.7 g (0.146 mole) of N-methyl benzamide and 400 ml. dry tetrahydrofuran. The reaction flask is immersed in an ice bath and cooled to an internal temperature of 5°C. Stirring is initiated and 204 ml. of 1.6 M. n-butyl lithium (~0.321 mole) in hexane is added dropwise over about 1 hour maintaining the temperature below 8°C. The resulting dilithio salt is stirred at 5°C. for an additional hour and then a solution of 40 g. (0.146 mole) of 4'-chloro-2-dimethylaminomethyl benzophenone in 500 ml. tetrahydrofuran is added dropwise over about 1 hour maintaining the temperature between -10 to 10°C. The resulting mixture is stirred at 5°C. for 1 hour longer and 150 ml. of saturated ammonium chloride is added maintaining the temperature at about 10°C. The layers are separated and the organic phase dried over ahydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give α-(4-chlorophenyl)-α-(2-dimethylaminomethyl phenyl)-α-hydroxy-N-methyl-o-toluamide; m.p. 154°-156°C.

後処理

  1. customTo a flask equipped with a stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. customThe reaction flask is immersed in an ice bath
  4. temperaturemaintaining the temperature below 8°C
  5. temperaturemaintaining the temperature between -10 to 10°C
  6. stirringThe resulting mixture is stirred at 5°C. for 1 hour longer
  7. temperaturemaintaining the temperature at about 10°C
  8. customThe layers are separated
  9. dry with materialthe organic phase dried over ahydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe residue is crystallized from ether

出典と根拠

ORDレコード
ord-59ede42cd4d74e42b5dd26f780f92a1b
出典データセット
uspto-grants-1976_03
特許番号
US03944570

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