Ethyl Glycolate → 3-(Hydroxymethyl)-6-[3-(trifluoromethyl)-phenyl]-1,2,4-triazolo[4,3-b]pyridazine

HRID 443505Notes

Reaction equation

HRID 443505 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:7][CH:8]=1)[NH2:2].[C:19](OCC)(=O)[CH2:20][OH:21]>C(O)CCC>[OH:21][CH2:20][C:19]1[N:4]2[N:5]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[CH:7]=[CH:8][C:3]2=[N:1][N:2]=1

Participants

4

Reactant 2

HCID 12184Ethyl GlycolateHCID 127268553-Hydrazinyl-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 234675663-(Hydroxymethyl)-6-[3-(trifluoromethyl)-phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.3 g. of 3-hydrazino-6-[3-(trifluoromethyl)phenyl]pyridazine, 188 g. of ethyl glycolate and 40 ml. of n-butyl alcohol is heated at reflux temperature for 18 hours. The mixture is evaporated in vacuo. To the residue is added dichloromethane and hexane. The mixture is filtered to give 2.0 g. of cream colored crystals. Recrystallization from ethyl acetate gives the product of the Example as off-white crystals, m.p. 224°-226° C.

Workup

  1. additionA mixture of 2.3 g
  2. temperatureat reflux temperature for 18 hours
  3. customThe mixture is evaporated in vacuo
  4. additionTo the residue is added dichloromethane and hexane
  5. filtrationThe mixture is filtered
  6. customto give 2.0 g
  7. customRecrystallization from ethyl acetate
  8. customgives the product of the Example as off-white crystals, m.p. 224°-226° C.

Sources & evidence

ORD record
ord-d3320f268d0a400ba86bfbe4f50c42f2
Source dataset
uspto-grants-1981_04
Patent number
US04260755

Reaction notes

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