Benzophenone imine → HCID 20071795, compound

HRID 981241Notes

Reaction equation

HRID 981241 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N[CH2:17][C:18]([O:20][C:21]([CH3:31])([CH3:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:19].[Cl-].[Cl-].[Ca+2]>C(Cl)Cl>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][CH2:17][C:18]([O:20][C:21]([CH3:31])([CH3:30])[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[O:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 136809Benzophenone imineHCID 5284359Calcium ChlorideHCID 20071796HCID 20071796, compound

Product 1

HCID 20071795HCID 20071795, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzophenone imine (0.8 g, 2.9 mmol) and finely ground 1-(4-chlorophenyl)-2-methyl-2-propyl glycinate hydrochloride and 10 ml of CH2Cl2 were stirred at room temperature over night with the exclusion of moisture (CaCl2 tube). The reaction mixture was filtered to remove NH4Cl, and evaporated to dryness. The residue was taken up in 10 ml of ether, washed with water and dried. Filtration and removal of the solvent were followed by flash chromatography on SiO2 saturated with NH3 (methanol/NH3) with hexane: ethyl acetate 97:3 as eluent to yield 0.8 g (63%) of 1-(4-chlorophenyl)-2-methyl-2-propyl N-(diphenylmethylene)glycinate. 1H NMR (CDCl3, 60 MHz) δppm 7.5(m, 10, arom), 4.2(s, 2, N-CH2), 3.1(s, 2, benzylic), 1.5(s, 6, C(CH3)2).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove NH4Cl
  3. customevaporated to dryness
  4. washwashed with water
  5. customdried
  6. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-7f2927e3cbe94a2a834d0105f9f656a2
Source dataset
uspto-grants-1991_02
Patent number
US04990534

Reaction notes

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