Dimethylformamide → HCID 13078278, compound

HRID 237131Notes

Reaction equation

HRID 237131 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:29])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[N:17]1[C:21]([CH2:22][NH2:23])=[N:20][C:19]([C:24](=[O:28])[N:25]([CH3:27])[CH3:26])=[N:18]1.[Cl:30][CH2:31][C:32](Cl)=[O:33].CN(C)C=O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:29])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[N:17]1[C:21]([CH2:22][NH:23][C:32](=[O:33])[CH2:31][Cl:30])=[N:20][C:19]([C:24](=[O:28])[N:25]([CH3:26])[CH3:27])=[N:18]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21315212HCID 21315212, compound

Product 1

HCID 13078278HCID 13078278, compoundYield 1,084.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

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. customto give a solution, which
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. additionThe residue is treated with ethanol/n-hexane

Sources & evidence

ORD record
ord-ff7876eb624d43b0a45c5b60ce971c9b
Source dataset
uspto-grants-1979_06
Patent number
US04159374

Reaction notes

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