Dimethyl 3-oxoadipate → HCID 178500002, compound

HRID 1755917Notes

Reaction equation

HRID 1755917 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH3:7])[NH:4][N:3]=1.O=[C:9]([CH2:15][CH2:16][C:17](OC)=[O:18])[CH2:10][C:11]([O:13][CH3:14])=[O:12]>>[CH3:7][C:5]1[N:6]=[C:2]2[NH:1][C:15]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:16][C:17](=[O:18])[N:3]2[N:4]=1

Participants

3

Reactant 2

HCID 79561Dimethyl 3-oxoadipateHCID 2346103-Amino-5-methyl-4H-1,2,4-triazole

Product 1

HCID 178500002HCID 178500002, compoundYield 70.6%

Conditions

Temperature
160 °C

Procedure

3-Amino-5-methyl-1H-s-triazole (19.8 g) (about 0.12 mol) (about 70%) and 30 g (0.16 mol) of dimethyl 3-oxo-adipate are melted together while gassing with argon for 1 hour in a bath heated at 160° C. In so doing, the volatile products are removed in a water-jet vacuum. After cooling the solid residue is dissolved in dichloromethane/methanol (1:1 v/v). The turbid yellowish solution is filtered and concentrated. The crystals which thereby result are filtered off under suction and washed with ethanol, subsequently with diethyl ether. There are obtained 20 g of methyl 4,7-dihydro-2-methyl-7-oxo-s-triazolo[1,5-a]pyrimidine-5-propionate as a white crystals of melting point 222°-225° C.

Workup

  1. customthe volatile products are removed in a water-jet vacuum
  2. temperatureAfter cooling the solid residue
  3. dissolutionis dissolved in dichloromethane/methanol (1:1 v/v)
  4. filtrationThe turbid yellowish solution is filtered
  5. concentrationconcentrated
  6. customThe crystals which thereby result
  7. filtrationare filtered off under suction
  8. washwashed with ethanol, subsequently with diethyl ether

Sources & evidence

ORD record
ord-c05e71bb1cad4bd6856e1c63289c1105
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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