Phosphorus oxychloride → Ethyl 6-chloro-1,2,4-triazine-5-carboxylate

HRID 2076829Notes

Reaction equation

HRID 2076829 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=O)[NH:10][N:9]=[CH:8][N:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:15]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]=[N:10][C:11]=1[Cl:15])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 117152386-Oxo-1,6-dihydro-[1,2,4]triazine-5-carboxylic acid ethyl ester

Product 1

HCID 72213151Ethyl 6-chloro-1,2,4-triazine-5-carboxylateYield 90%

Procedure

6-Oxo-1,6-dihydro-[1,2,4]triazine-5-carboxylic acid ethyl ester (115 mg, 0.68 mmol) in POCl3 (1.5 ml) was heated to 100° C. for 2 h. All volatiles were then removed and the remaining residue was diluted with cold CHCl3 and carefully neutralized with sat. NaHCO3-solution. This mixture was extracted with cold CHCl3. The organic phase was then washed with cold brine, dried (Na2SO4) and evaporated to give the crude title compound (115 mg, 90%) as brown gum, which was used in the next reaction step without further purification. MS: m/e=188.2 [M+H+].

Workup

  1. customAll volatiles were then removed
  2. additionthe remaining residue was diluted with cold CHCl3
  3. extractionThis mixture was extracted with cold CHCl3
  4. washThe organic phase was then washed with cold brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-68918494679341918845bb9785d0d5fb
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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