Ethyl Acetate → 5-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone

HRID 614043

Reaction equation

HRID 614043 reaction equation
[C:1]1(=[O:15])[N:5]([CH2:6][C:7](Cl)=[O:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12.Br.Br.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([N:33]2[C:37]([CH3:38])=[N:36][N:35]=[C:34]2[CH2:39][NH2:40])=[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>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([N:33]2[C:37]([CH3:38])=[N:36][N:35]=[C:34]2[CH2:39][NH:40][C:7](=[O:8])[CH2:6][N:5]2[C:4](=[O:10])[C:3]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]3[C:1]2=[O:15])=[C:23]([CH:32]=1)[C:24]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:25]

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 155678715-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenoneYield 69.4%

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-[3-(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-7b823883da4a4fdf95457f201a2c32df
Source dataset
uspto-grants-1979_03
Patent number
US04143048

Linked notes

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