Amitrole → HCID 178515486, compound

HRID 923342

Reaction equation

HRID 923342 reaction equation
[N:1]1[NH:2][C:3]([NH2:6])=[N:4][CH:5]=1.[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[C:14]([C:17](=O)[CH2:18][C:19](OCC)=[O:20])[CH:15]=[CH:16][C:8]1=2>C(O)(=O)C>[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[C:14]([C:17]3[NH:6][C:3]4[N:2]([N:1]=[CH:5][N:4]=4)[C:19](=[O:20])[CH:18]=3)[CH:15]=[CH:16][C:8]1=2

Participants

4

Reactant 2

HCID 1639AmitroleHCID 15315318Ethyl 2,3-dihydro-β-oxo-1,4-benzodioxin-6-propanoate

Product 1

HCID 178515486HCID 178515486, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2H-1,2,4-triazol-3-amine (200 mg, 2.38 mmol, 1.00 equiv), acetic acid (3 mL), and ethyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxopropanoate (600 mg, 2.40 mmol, 1.01 equiv) was stirred for 24 hr at 120° C. and then concentrated to dryness. The resulting solid was washed with MeOH and collected by filtration. The solid was dissolved in 15 mL of NH4OH (aq.) and filtered. The filtrate was adjusted to pH 5 with HOAc. The resulting solid was collected by filtration and washed with water. The solid was dried to get 95 mg (15%) of 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. washThe resulting solid was washed with MeOH
  3. filtrationcollected by filtration
  4. dissolutionThe solid was dissolved in 15 mL of NH4OH (aq.)
  5. filtrationfiltered
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customThe solid was dried

Sources & evidence

ORD record
ord-bde312b457114b68bc8a3ac5eae6bfc4
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Linked notes

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