Potassium Carbonate → HCID 12942564, compound

HRID 2198399Notes

Reaction equation

HRID 2198399 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[N:10][C:9]([OH:12])=[N:8]1.C(=O)([O-])[O-].[K+].[K+].[P:19](=[S:25])(Cl)([O:22][CH3:23])[O:20][CH3:21]>C(#N)C.CN(C)C1C=CN=CC=1>[P:19](=[S:25])([O:12][C:9]1[N:10]=[CH:11][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=1)([O:22][CH3:23])[O:20][CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 17304Dimethyl phosphorochloridothionateHCID 178518009HCID 178518009, compound

Product 1

HCID 12942564HCID 12942564, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent3×

Procedure

A mixture of 8.10 g (0.05 m) of 1-(2-pyridinyl)-1H-1,2,4-triazol-3-ol and 8.29 g (0.06 m) of powdered potassium carbonate in 150 ml of acetonitrile was vigorously stirred together for 21/2 hours at 40°-50° C. To this mixture was successively added a solution of 0.29 g (0.0024 m (5 mole percent)) of 4-dimethylaminopyridine in 25 ml of acetonitrile followed by a solution of 7.94 g (0.048 m) of O,O-dimethyl phosphorochloridothioate in 25 ml of acetonitrile. After a 2 hour period, the reaction was complete and the reaction mixture was filtered and evaporated to dryness. The oil which remained as a residue was triturated with hexane and solidification occurred. The solid, crude O,O-dimethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate product was recovered in a yield of 11.3 g (82 percent of theoretical) and melted at 88°-91° C. The product after recrystallization from methyl cyclohexane melted at 95°-96° C. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 37.68, 3.91 and 19.51 percent, respectively, as compared with the theoretical contents of 37.76, 3.87 and 19.58 percent, respectively, as calculated for the named compound. (Compound 6).

Workup

  1. waitAfter a 2 hour period
  2. filtrationthe reaction mixture was filtered
  3. customevaporated to dryness
  4. customwas triturated with hexane and solidification
  5. customThe solid, crude O,O-dimethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate product was recovered in a yield of 11.3 g (82 percent of theoretical) and melted at 88°-91° C
  6. customThe product after recrystallization from methyl cyclohexane melted at 95°-96° C

Sources & evidence

ORD record
ord-0971cdf4d5b244d29b5548b52a163e58
Source dataset
uspto-grants-1982_11
Patent number
US04357327

Reaction notes

Loading…