Dimethyl Sulfoxide → HCID 70620721, compound

HRID 2420468Notes

Reaction equation

HRID 2420468 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])=[CH:4][CH:3]=1.[OH-:26].[Na+].CS(C)=[O:30].Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39]Cl.[OH2:41]>>[C:2]([OH:1])(=[O:30])/[CH:7]=[CH:6]\[C:5]([OH:41])=[O:26].[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([NH:11][CH2:12][CH:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962Water2×HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 20311664HCID 20311664, compound

Product 1

HCID 70620721HCID 70620721, compound

Procedure

The mixture of 3,4 g of 1-(4-hydroxyphenyl)-2-(2,2,-diphenylethylamino)-propane, 1.0 g of sodium hydroxide in 5 ml of water, and 50 ml of dimethylsulphoxide is warmed to 60°, and 1.7 g of 2-pyridylmethyl chloride hydrochloride are added. The mixture is stirred overnight at ambient temperature, then diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried, evaporated and the residue dissolved in 30 ml of warm methanol. The solution is treated with 1.1 g of maleic acid, cooled and then treated with 30 ml of diethyl ether. The precipitate formed is washed with ethyl acetate and dried, to afford the dl-1-[4-(2-pyridylmethoxy)-phenyl]-2-(2,2-diphenylethylamino)-propane maleate, melting at 167°-169°.

Workup

  1. temperatureis warmed to 60°
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. customdried
  5. customevaporated
  6. dissolutionthe residue dissolved in 30 ml of warm methanol
  7. additionThe solution is treated with 1.1 g of maleic acid
  8. temperaturecooled
  9. additiontreated with 30 ml of diethyl ether
  10. customThe precipitate formed
  11. washis washed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-b6a58e9be639442ab8c7b234c2ff4f4e
Source dataset
uspto-grants-1978_08
Patent number
US04110457

Reaction notes

Loading…