Ethyl Acetate → Benzophenone

HRID 1391284Notes

Reaction equation

HRID 1391284 reaction equation
C1(=O)N(CC(Cl)=O)C(=O)C2=CC=CC=C12.Br.Br.Cl[C:19]1[CH:20]=[CH:21][C:22](N2C(C)=NN=C2CN)=[C:23]([CH:32]=1)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1C=CC=CC=1.CN(C)C=O>[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])[C:23]1[CH:32]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 213257365-chloro-2-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide

Product 1

HCID 3102BenzophenoneYield 195.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-phthalimidoacetyl chloride (1.5 g) in benzene (20 ml) and dimethylformamide (10 ml), 5-chloro-2-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide (2.3 g) is added under ice cooling and stirring, and the temperature within the flask is gradually returned to room temperature. The reaction mixture is allowed to stand at room temperature, neutralized with saturated aqueous sodium bicarbonate, and shaken with ethyl acetate. The precipitated crystals are filtered, washed with methanol and dried to give 5-chloro-2-[2-phthalimidoacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone (1.68 g) as crystals melting at 251°-253° C.

Workup

  1. customis gradually returned to room temperature
  2. customto stand at room temperature
  3. filtrationThe precipitated crystals are filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-3c1c18cdeaff43edba1eb2a2d67fc856
Source dataset
uspto-grants-1979_02
Patent number
US04141901

Reaction notes

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