Benzene → HCID 13243693, compound

HRID 442099Notes

Reaction equation

HRID 442099 reaction equation
[NH2:1][N:2]1[C:11]([OH:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:19])[CH:9]=2)[N:4]=[CH:3]1.[Cl:20][CH2:21]C(O)=O.[CH:25]1C=CC=CC=1>>[Br:19][C:8]1[CH:7]=[CH:6][C:5]([N:4]2[CH:25]=[N:1][N:2]=[C:3]2[CH2:21][Cl:20])=[C:10]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:18])[CH:9]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 300Chloroacetic AcidHCID 13243689HCID 13243689, compound

Product 1

HCID 13243693HCID 13243693, compound

Procedure

A mixture of a solution of 0.94 g of the thus obtained di-(chloroacetyl) derivative of 3-amino-6-bromo-4-hydroxy-4-(2-pyridyl)-3,4-dihydroquinazoline in 19 ml. of benzene and 0.4 g of monochloroacetic acid is refluxed for 30 minutes. Then, the resulting benzene layer is washed with water and separated from the mixture. After evaporation of benzene under reduced pressure, the residue is washed with a mixture of methanol and isopropyl ether to give 4-[4-bromo-2-(2-pyridinecarbonyl)phenyl]-3-chloromethyl-4H-1,2,4-triazole as crystals. Recrystallization from ethyl acetate gives colorless crystals, melting at 146° to 147° C.

Workup

  1. washThen, the resulting benzene layer is washed with water
  2. customseparated from the mixture
  3. customAfter evaporation of benzene under reduced pressure
  4. washthe residue is washed with a mixture of methanol and isopropyl ether

Sources & evidence

ORD record
ord-e2452949e1354afdaa2324769c8eeb53
Source dataset
uspto-grants-1977_08
Patent number
US04044129

Reaction notes

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