Dimethyl Sulfoxide → HCID 70620955, compound

HRID 2420470Notes

Reaction equation

HRID 2420470 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.[OH-:27].[Na+].CS(C)=[O:31].[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:40]Cl)=[N:38][CH:39]=1.[OH2:42]>>[C:2]([OH:1])(=[O:31])/[CH:7]=[CH:6]\[C:5]([OH:42])=[O:27].[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:40][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH2:13][CH:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:10])=[CH:6][CH:7]=2)=[N:38][CH:39]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 14798Sodium HydroxideHCID 5880562-(Chloromethyl)-5-methylpyridineHCID 130652814-{2-[(3,3-Diphenylpropyl)amino]propyl}phenol

Product 1

HCID 70620955HCID 70620955, compound

Procedure

The mixture of 21.76 g of dl-1-(4-hydroxyphenyl)-2-(3,3-diphenylpropylamino)-propane, 6.3 ml of 10 N aqueous sodium hydroxide and 100 ml of dimethylsulphoxide is stirred at 60° for 2 hours, whereupon 8.91 g of 5-methyl-2-pyridylmethyl chloride are added. The whole is stirred at ambient temperature for 24 hours, diluted with 400 ml of water and extracted with methylene chloride. The extract is dried, evaporated, the residual oil taken up in isopropanol and the solution acidified with maleic acid in isopropanol until the pH of 5 is reached, to yield the dl-1-[4-(5-methyl-2-pyridylmethoxy)-phenyl]-2-(3,3-diphenylpropylamino)propane maleate, melting at 155°-157°.

Workup

  1. additionare added
  2. extractionextracted with methylene chloride
  3. customThe extract is dried
  4. customevaporated

Sources & evidence

ORD record
ord-d344c61602c945d581a4f0b1d3be333a
Source dataset
uspto-grants-1978_08
Patent number
US04110457

Reaction notes

Loading…