HCID 13078264, compound → HCID 21315212, compound

HRID 237130Notes

Reaction equation

HRID 237130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:38])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21][NH:22]C(OCC2C=CC=CC=2)=O)=[N:19][C:18]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])=[N:17]1.[BrH:39].C(O)(=O)C>CCOCC>[BrH:39].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:38])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21][NH2:22])=[N:19][C:18]([C:33](=[O:37])[N:34]([CH3:35])[CH3:36])=[N:17]1

Participants

4

Reactant 2

HCID 13078264HCID 13078264, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 21315212HCID 21315212, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2',5-dichloro-2-(3-dimethylcarbamoyl-5-carbobenzoxyaminomethyl-1,2,4-triazol- 1-yl)benzophenone (3.6 g) and 30% hydrogen bromide-acetic acid (9 ml) is stirred at room temperature for 2 hours. The reaction mixture is mixed with ether, and the precipitate is isolated by decantation and washed thrice with ether, whereby 2',5-dichloro-2-(3-dimethylcarbamoyl-5-aminomethyl-1,2,4-triazol- 1-yl)-benzophenone hydrobromide is obtained. This hydrobromide (1.2 g) is added to a solution of chloroacetyl chloride (1.2 g) in benzene (40 ml) to give a solution, which is mixed with dimethylformamide (20 ml). The resultant mixture is stirred at room temperature for 3 hours. The reaction mixture is mixed with ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer is separated, washed with water, dried, and evaporated under reduced pressure to remove the solvent. The residue is treated with ethanol/n-hexane to give 2',5-dichloro-2-[3-dimethylcarbamoyl-5-(2-chloroacetylamino)methyl-1,2,4-triazol- 1-yl]-benzophenone (12.9 g), which is recrystallized from ethyl acetate to give colorless needles melting at 80°-82° C.

Workup

  1. customthe precipitate is isolated by decantation
  2. washwashed thrice with ether

Sources & evidence

ORD record
ord-a232e55b26fe4becaa0095f7fab4db07
Source dataset
uspto-grants-1979_06
Patent number
US04159374

Reaction notes

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