Ethanol → 2-Amino-5-chloro-8-methoxy[1,2,4]triazolo[1,5-a]pyridine

HRID 1940928Notes

Reaction equation

HRID 1940928 reaction equation
Cl.NO.C([N:7](C(C)C)CC)(C)C.C(O)C.[Cl:16][C:17]1[N:22]=[C:21]([NH:23][C:24]([NH:26]C(OCC)=O)=S)[C:20]([O:32][CH3:33])=[CH:19][CH:18]=1>O>[NH2:7][C:24]1[N:23]=[C:21]2[C:20]([O:32][CH3:33])=[CH:19][CH:18]=[C:17]([Cl:16])[N:22]2[N:26]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21464341N-(6-Chloro-3-methoxy-2-pyridinyl)-N'-carboethoxythiourea

Product 1

HCID 183661952-Amino-5-chloro-8-methoxy[1,2,4]triazolo[1,5-a]pyridineYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (9.6 g, 138 mmol) and diisopropylethylamine (14.4 mL, 10.7 g, 83 mmol) were mixed with ethanol (300 mL) for a few minutes and then N-(6-chloro-3-methoxy-2-pyridinyl)-N'-carboethoxythiourea (7.6 g, 27.5 mmol) was added with stirring. The resulting mixture was stirred at room temperature for 20 min and then heated to reflux for 3 hours. The volatile components were removed by evaporation and the residue obtained was mixed with water. The resulting slurry was filtered and the solids collected were washed with ether, a small amount of methanol, and finally hexane and were then dried. The title compound (3.2 g) was obtained as a tan powder melting at 207°-208° C.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 20 min
  2. temperatureheated
  3. temperatureto reflux for 3 hours
  4. customThe volatile components were removed by evaporation
  5. customthe residue obtained
  6. filtrationThe resulting slurry was filtered
  7. customthe solids collected
  8. washwere washed with ether
  9. dry with materiala small amount of methanol, and finally hexane and were then dried

Sources & evidence

ORD record
ord-2e93278c6de64f08ad22b94276dcdead
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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