Acetic Anhydride → 5-Amino-3-methylcarbonylamino-6-(3,4-dichlorophenyl)-1,2,4-triazine

HRID 1441014Notes

Reaction equation

HRID 1441014 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)=[C:6]([NH2:8])[N:7]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>CN(C)C1C=CN=CC=1.O1CCOCC1>[NH2:8][C:6]1[N:7]=[C:2]([NH:1][C:17]([CH3:18])=[O:19])[N:3]=[N:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15332575HCID 15332575, compound

Product 1

HCID 153325765-Amino-3-methylcarbonylamino-6-(3,4-dichlorophenyl)-1,2,4-triazine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

A stirring mixture of 5.0 grams (0.020 mole) of 3,5-diamino-6-(3,4-dichlorophenyl)-1,2,4-triazine (Compound 24; disclosed in J. Med. Chem., 1972, Vol. 15, No 8. 859-861), 2.0 grams (0.020 mole) of acetic anhydride and 0.01 gram (catalyst) of 4-dimethylaminopyridine in 40 mL of dioxane is heated at reflux for about two hours. The mixture is cooled and concentrated under reduced pressure to a residue. The residue is purified by column chromatography on silica gel, yielding 5-amino-3-methylcarbonylamino-6-(3,4-dichlorophenyl)-1,2,4-triazine.

Workup

  1. temperatureat reflux for about two hours
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d3bebb3d5a3a4bfa8f71713c7d9247dc
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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