Phosphorus oxychloride → 7-Chloro-5-methyltetrazolo[1,5-a]pyrimidine

HRID 1089524Notes

Reaction equation

HRID 1089524 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]2[N:9]=[N:10][N:11]=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[Cl:14][C:6]1[N:5]2[N:9]=[N:10][N:11]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429190HCID 178429190, compound

Product 1

HCID 148526107-Chloro-5-methyltetrazolo[1,5-a]pyrimidineYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 67.88 g (0.45 mole) of 5-methyl-7-hydroxytetrazolo[1,5-a]pyrimidine and 300 ml of phosphorus oxychloride was stirred for 1.5 hours in a bath of 100° C. and then concentrated. The residue obtained was dissolved in 600 ml of chloroform, ice-cooled and then washed with water, followed by drying over anhydrous magnesium sulfate to evaporate the solvent. The set residue was collected by filtration with addition of n-hexane and dried to obtain 70.2 g of the title compound (Yield: 92%).

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. temperatureice-cooled
  4. washwashed with water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. customto evaporate the solvent
  7. filtrationThe set residue was collected by filtration with addition of n-hexane
  8. customdried

Sources & evidence

ORD record
ord-e4caaf4c6dfe478284213619b28d256e
Source dataset
uspto-grants-1990_10
Patent number
US04966900

Reaction notes

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