alpha-(4-chlorophenyl)-alpha-(2-dimethylaminomethyl phenyl)-alpha-hydroxy-N-methyl-o-toluamide → HCID 54539385, compound

HRID 267749

Reaction equation

HRID 267749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][N:27]([CH3:29])[CH3:28])([OH:19])[C:9]2[C:10]([C:15](NC)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][N:27]([CH3:29])[CH3:28])[C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:15](=[O:16])[O:19]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 21554039alpha-(4-chlorophenyl)-alpha-(2-dimethylaminomethyl phenyl)-alpha-hydroxy-N-methyl-o-toluamide

Product 1

HCID 54539385HCID 54539385, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 40.8 g. (0.1 mole of α-(4-chlorophenyl)-α-(2-dimethylaminomethyl phenyl)-α-hydroxy-N-metyl-o-toluamide and 200 ml. o-dichlorobenzene is refluxed for 20 hours, cooled and the solvent is removed in vacuo. The residue is triturated with ether and the resulting solid is recrystallized from ether-methylene chloride (1:1) to give 3-(4-chlorophenyl)-3-(2-dimethylaminomethyl phenyl) phthalide; m.p. 138.5° - 140°C.

Workup

  1. additionA mixture of 40.8 g
  2. temperaturecooled
  3. customthe solvent is removed in vacuo
  4. customThe residue is triturated with ether
  5. customthe resulting solid is recrystallized from ether-methylene chloride (1:1)

Sources & evidence

ORD record
ord-a442e4a183144b26823e3f24212e1708
Source dataset
uspto-grants-1976_03
Patent number
US03944570

Linked notes

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