Acetonitrile → HCID 23350234, compound

HRID 2057856Notes

Reaction equation

HRID 2057856 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[N:11]1.Br[CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:21][CH2:22][Cl:23])=[CH:4][C:3]=1[N:10]1[C:18](=[O:19])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[N:11]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 231942032-(2,4-Dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 23350234HCID 23350234, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 Parts of 2-(2,4-dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one prepared as described above in Example 3, 1.4 parts of 1-bromo-2-chloroethane, 1.5 parts of anhydrous potassium carbonate and 20 parts of dry acetonitrile were combined and refluxed for 6 hours followed by stirring for 72 hours at room temperature. The reaction mixture was poured into 200 parts of water. The aqueous suspension of the product was extracted three times with 200 parts of methylene chloride. The organic extracts of the product were dried with anhydrous sodium sulfate. The solvent was stripped from the product at reduced pressure on a rotary evaporator. The resulting dark oil was crystallized from ether yielding 0.2 parts of a light brown solid with m.p. 148°-150°.

Workup

  1. temperaturerefluxed for 6 hours
  2. additionThe aqueous suspension of the product
  3. extractionwas extracted three times with 200 parts of methylene chloride
  4. dry with materialThe organic extracts of the product were dried with anhydrous sodium sulfate
  5. customThe solvent was stripped from the product at reduced pressure on a rotary evaporator
  6. customThe resulting dark oil was crystallized from ether yielding 0.2 parts of a light brown solid with m.p. 148°-150°

Sources & evidence

ORD record
ord-4afa548d8bbb4b52abc712a02d111ff0
Source dataset
uspto-grants-1980_07
Patent number
US04213773

Reaction notes

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