Hydroxylamine → 8-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

HRID 2368034Notes

Reaction equation

HRID 2368034 reaction equation
NO.C([N:6](CC)C(C)C)(C)C.[Br:12][C:13]1[C:14]([NH:19][C:20]([NH:22]C(OCC)=O)=S)=[N:15][CH:16]=[CH:17][CH:18]=1>CO.C(O)C>[Br:12][C:13]1[C:14]2[N:15]([N:6]=[C:20]([NH2:22])[N:19]=2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 59199107Ethyl aminon-(3-bromopyridin-2-YL)methanethiocarbamate

Product 1

HCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Hydroxylamine (58.5 g, 842 mmol) and N,N-diisopropylethylamine (65.3 g, 86.3 mL, 505 mmol) were dissolved in methanol (200 mL) and ethanol (200 mL). N-(3-Bromo-pyridin-2-yl)-N′-ethoxycarbonyl-thiourea (51.2 g, 168 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour and then at 60° C. for 3 hours. The white precipitate was filtered off and triturated with water for 25 minutes, filtered and triturated two times with diethyl ether. The solid was dried by co-evaporation with toluene and dried in vacuum. The title compound was obtained as a white solid (27.9 g, 78%).

Workup

  1. waitat 60° C. for 3 hours
  2. filtrationThe white precipitate was filtered off
  3. customtriturated with water for 25 minutes
  4. filtrationfiltered
  5. customtriturated two times with diethyl ether
  6. dry with materialThe solid was dried by co-evaporation with toluene
  7. customdried in vacuum

Sources & evidence

ORD record
ord-c5bdff5b99dd4a0d95158287c5960a77
Source dataset
uspto-grants-2014_04
Patent number
US08703763B2

Reaction notes

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