Sodium Chloride → Benzhydryl 2-phthalimidooxyacetate

HRID 234180Notes

Reaction equation

HRID 234180 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[C:6]1([C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N+]=[N-])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].[Cl-].[Na+]>CO.C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[C:26]1(=[O:27])[N:22]([O:21][CH2:2][C:3]([O:5][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]12

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 6227Bromoacetic AcidHCID 10665N-HydroxyphthalimideHCID 612301,1'-(Diazomethylene)bis(benzene)

Product 1

HCID 12784561Benzhydryl 2-phthalimidooxyacetate

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromoacetic acid (10.45 g) was dissolved in methanol (30 ml). To the solution was added an equivalent volume of diphenyl diazomethane in ethyl acetate at 45° C., and the reaction mixture was stirred at the same temperature for an hour. The solution was washed with 5% aqueous sodium bicarbonate and a saturated aqueous sodium chloride, and then dried over magnesium sulfate. The solution was evaporated in vacuo to give an oily product. This oil was dissolved in N,N-dimethylformamide (60 ml). To the solution was added N-hydroxyphthalimide (11.7 g) and triethylamine (15.1 ml), and the reaction mixture was stirred at ambient temperature for an hour. The resultant mixture was poured into a saturated aqueous sodium chloride (500 ml). The precipitates were collected by filtration, washed with water, and then dissolved in methylene chloride (700 ml). The solution was washed with a saturated aqueous sodium chloride, dried over magnesium sulfate, and then evaporated under reduced pressure to give benzhydryl 2-phthalimidooxyacetate (20.4 g), mp 173°-175° C.

Workup

  1. washThe solution was washed with 5% aqueous sodium bicarbonate
  2. dry with materiala saturated aqueous sodium chloride, and then dried over magnesium sulfate
  3. customThe solution was evaporated in vacuo
  4. customto give an oily product
  5. stirringthe reaction mixture was stirred at ambient temperature for an hour
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. dissolutiondissolved in methylene chloride (700 ml)
  9. washThe solution was washed with a saturated aqueous sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-982356e6fe5d4adfba7c33d448fbc3ab
Source dataset
uspto-grants-1997_01
Patent number
US05594132

Reaction notes

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