Hydrochloric Acid → HCID 20308944, compound

HRID 1763946Notes

Reaction equation

HRID 1763946 reaction equation
[CH2:1]([NH:8][C:9](=[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](=[O:19])[O:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[Na].[ClH:28]>O1CCOCC1.O>[Cl-:28].[CH2:1]([NH:8][CH:9]([CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](=[O:19])[O:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418435HCID 178418435, compoundHCID 178519175HCID 178519175, compound

Product 1

HCID 20308944HCID 20308944, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4.90 g (0.015 mole) of α-benzylamino-benzylidenephthalide (R = C6H5 ; R' = H; R" =C6H5CH2 ; X = H) is dissolved in 40 ml of absolute dioxane, and dry hydrogen chloride is bubbled through the solution. 10 to 15 minutes of this procedure causes the dioxane solution to grow turbid, with fine crystals precipitating out. 2.84 g (0.075 mole) of sodium boron hydride is added to this suspension. The solution is maintained at room temperature for 2 days, after which the excess of the reducing agent is decomposed with weak hydrochloric acid, the acid solution is diluted with a triple amount of water, neutralized with alkali hydroxide and extracted with ether. The ether extract is dried over magnesium sulfate, filtered off and saturated with dry hydrogen chloride. The resultant white precipitate is filtered off to yield 3.60 g (65%) of 1-benzylamino-1-phthalidyl-1-phenylmethane chloride. Crystallization from absolute methanol with absolute ether added yields 3.10 g (56% of the theoretical) of a product with a melting point of 255° to 257° C.

Workup

  1. customdry hydrogen chloride is bubbled through the solution
  2. custom10 to 15 minutes of this procedure
  3. customwith fine crystals precipitating out
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered off and saturated with dry hydrogen chloride
  8. filtrationThe resultant white precipitate is filtered off

Sources & evidence

ORD record
ord-2b78c313b9634558a4d4c8b2300f0ec4
Source dataset
uspto-grants-1978_09
Patent number
US04113948

Reaction notes

Loading…