Acetonitrile → HCID 86737096, compound

HRID 2057857Notes

Reaction equation

HRID 2057857 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.[CH2:20]([O:22][C:23](=O)[CH:24](Br)[CH3:25])[CH3:21].C(=O)([O-])[O-:29].[K+].[K+].C(#N)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:23]([O:22][CH2:20][CH3:21])[CH:24]=[C:25]=[O:29])=[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 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 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 86737096HCID 86737096, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.1 Parts of 2-(2,4-dichloro-5-hydroxy phenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one prepared as described in Example 3, 12.1 parts of ethyl-2-bromopropionate, 9.3 parts of anhydrous potassium carbonate and 100 parts of dry acetonitrile were refluxed for 5 hours. The reaction was cooled and poured into 250 parts of H2O. The aqueous suspension of product was extracted three times with 250 parts of methylene chloride and then the solution was dried with anhydrous sulfate. The solvent was removed on a rotary evaporator at reduced pressure. The glassy residue was crystallized from ethyl acetate-ether mixture. The yield was 16.0 parts of a light brown solid with m.p. 136°-138°.

Workup

  1. temperaturewere refluxed for 5 hours
  2. temperatureThe reaction was cooled
  3. additionThe aqueous suspension of product
  4. extractionwas extracted three times with 250 parts of methylene chloride
  5. dry with materialthe solution was dried with anhydrous sulfate
  6. customThe solvent was removed on a rotary evaporator at reduced pressure
  7. customThe glassy residue was crystallized from ethyl acetate-ether mixture

Sources & evidence

ORD record
ord-fb79593a7d9546118a68c915e7e90fb0
Source dataset
uspto-grants-1980_07
Patent number
US04213773

Reaction notes

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