N-Methylbenzamide → HCID 21554039, 화합물

HRID 267748

반응식

HRID 267748 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 21554039HCID 21554039, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59ede42cd4d74e42b5dd26f780f92a1b
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03944570

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