Diisopropylethylamine → HCID 18769956, compound

HRID 1058554Notes

Reaction equation

HRID 1058554 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:11][C:12]([NH:14]C(=O)OCC)=S)=[N:5][C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.Cl.NO.C([N:26](C(C)C)CC)(C)C>C(O)C>[NH2:26][C:12]1[N:11]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[C:6]([O:9][CH3:10])[N:5]2[N:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86585498HCID 86585498, compound

Product 1

HCID 18769956HCID 18769956, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 58.4 g (0.21 mole) of ethyl [(3,6-dimethoxypyridin-2-yl)amino]carbonothioylcarbamate, 70 g (1 mole) of hydroxylamine hydrochloride and 105 mL (0.6 mole) of diisopropylethylamine in 1 liter of ethanol was heated to reflux for 12 hr. After cooling, the resulting solution was evaporated to dryness under vacuum. Water (250 ml) and diethyl ether (100 ml) were added to the residue and the mixture was stirred for 15 min. The product was collected by filtration and dried under a vacuum at room temperature to give 25.2 g of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridine. mp 223-234° C. 1H NMR (DMSO-d6): δ 6.9 (d, 1H, j=8.7) 6.2 (d, 1H, j=8.4); 5.9 (s, 2H); 4.0 (s, 3H); 3.8 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hr
  3. temperatureAfter cooling
  4. customthe resulting solution was evaporated to dryness under vacuum
  5. additionWater (250 ml) and diethyl ether (100 ml) were added to the residue
  6. filtrationThe product was collected by filtration
  7. customdried under a vacuum at room temperature

Sources & evidence

ORD record
ord-04696104e8ab46afa98f799117c8408a
Source dataset
uspto-grants-2003_02
Patent number
US06518222B2

Reaction notes

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