Sulfuric Acid → HCID 15115297, compound

HRID 1451791Notes

Reaction equation

HRID 1451791 reaction equation
[C-:1]#[N:2].[Na+].S(=O)(=O)(O)[OH:5].[N+:9]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>C(O)(=O)C.C(OCCCC)CCC>[CH:1]([NH:2][C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:20])[CH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=1)=[O:5]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 53814216HCID 53814216, compound

Product 1

HCID 15115297HCID 15115297, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8909Butyl etherSolvent2×

Procedure

To a suspension of sodium cyanide (34.3 g, 0.7 mol) in glacial acetic acid (500 ml) and n-butylether (100 ml) at 0° C. was added portionwise concentrated sulphuric acid (200 ml). The ice bath was removed and a solution of 1-(3-nitrophenyl)-2-phenyl-1-propene (prepared from [(3-nitrophenyl)methylene]triphenylphosphorane and acetophenone, 0.5 mol) in n-butylether (100 ml) was added dropwise over a period of 2 hours, then the mixture stirred for 48 hours. The mixture was poured into 1000 ml ice, and extracted with chloroform. The extracts were washed with water, dried and evaporated to a solid residue which was stirred with hexane (500 ml), filtered and dried to give N-formyl-1-(3-nitrophenyl)-2-phenyl-2-propylamine. This was treated with fumaric acid in ethyl acetate/isopropanol to give the title compound in 97% yield. Mp 234°-235° C.

Workup

  1. customThe ice bath was removed
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. customdried
  5. customevaporated to a solid residue which
  6. stirringwas stirred with hexane (500 ml)
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7eb22c37fabf4638b41a1de4c4ab7ac8
Source dataset
uspto-grants-1997_02
Patent number
US05605916

Reaction notes

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