Benzene → HCID 13243693, compound

HRID 597353Notes

Reaction equation

HRID 597353 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 monochloro acetic acid is refluxed for 30 minutes. Then, the benzene layer is washed with water. 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. additionA mixture of a solution of 0.94 g
  2. washThen, the benzene layer is washed with water
  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-f4f1163dc3bd4a699d341f6bee4c06b8
Source dataset
uspto-grants-1977_03
Patent number
US04013763

Reaction notes

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