P-Toluic Acid → HCID 12774888, compound

HRID 848633Notes

Reaction equation

HRID 848633 reaction equation
[OH:1][CH2:2][N:3]1[C:8](=[O:9])[NH:7][C:6](=[O:10])[CH:5]=[N:4]1.[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:1][CH2:2][N:3]2[C:8](=[O:9])[NH:7][C:6](=[O:10])[CH:5]=[N:4]2)=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7470P-Toluic AcidHCID 12774884HCID 12774884, compound

Product 1

HCID 12774888HCID 12774888, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxymethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (1.00 g), p-methylbenzoic acid (0.95 g) and N,N-dicyclohexylcarbodiimide (2.90 g) are dissolved in pyridine, and the mixture is allowed to stand overnight. The reaction mixture is then evaporated to dryness to give a residue, which is extracted with chloroform. The chloroform extract is condensed to give an oil, which is purified by thin layer chromatography with silica gel and recrystallized from a mixture of ethanol/n-hexane. 2-(p-Methylbenzoyloxymethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 42) is thus obtained. Yield, 1.01 g (56%). M.P. 139.3° C.

Workup

  1. customThe reaction mixture is then evaporated to dryness
  2. customto give a residue, which
  3. extractionis extracted with chloroform
  4. extractionThe chloroform extract
  5. customcondensed
  6. customto give an oil, which
  7. customis purified by thin layer chromatography with silica gel
  8. customrecrystallized from a mixture of ethanol/n-hexane

Sources & evidence

ORD record
ord-a60834335df9425ca0b559e5dc232e0c
Source dataset
uspto-grants-1981_10
Patent number
US04297129

Reaction notes

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