HCID 13590330, compound → HCID 13590348, compound

HRID 1380055Notes

Reaction equation

HRID 1380055 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([N:17]=[C:18]([NH2:20])[N:19]=2)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=[N:6][CH:7]=1.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[C:3]2[N:4]([N:17]=[C:18]([NH:20][C:27](=[O:29])[CH3:28])[N:19]=2)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 13590330HCID 13590330, compoundHCID 22348678Acetic anhydride pyridine

Product 1

HCID 13590348HCID 13590348, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A 12.7 g portion of 8-methyl-5-(3-nitrophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2amine and 306 mg of 4-dimethylaminopyridine in 150 ml of pyridine:acetic anhydride (2:1) was refluxed with stirring for one hour. The solution was cooled and then evaporated to dryness. The residue was slurried in 100 ml of ether and the brown crystals collected. These were dissolved in 1200 ml of hot ethanol, filtered and the filtrate concentrated to 200 ml and cooled. The crystals were collected, giving 11.3 g of the desired product, mp 245°-247° C.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated to dryness
  3. customthe brown crystals collected
  4. dissolutionThese were dissolved in 1200 ml of hot ethanol
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated to 200 ml
  7. temperaturecooled
  8. customThe crystals were collected

Sources & evidence

ORD record
ord-03e9c98491414915819716b0bccbd0b8
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

Loading…