Triethylamine → HCID 12799320, compound

HRID 1902213Notes

Reaction equation

HRID 1902213 reaction equation
[C:1]([NH:3][C:4]([C:6]1[C:11]([NH2:12])=[N:10][C:9]([N:13]([CH3:15])[CH3:14])=[C:8]([Cl:16])[N:7]=1)=N)#[N:2].Cl.[NH2:18][OH:19].C(N(CC)CC)C.[Cl-].[Ca+2].[Cl-]>O.CO.O1CCCC1>[NH2:2][C:1]1[N:3]=[C:4]([C:6]2[C:11]([NH2:12])=[N:10][C:9]([N:13]([CH3:15])[CH3:14])=[C:8]([Cl:16])[N:7]=2)[O:19][N:18]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 5284359Calcium ChlorideHCID 178483075HCID 178483075, compound

Product 1

HCID 12799320HCID 12799320, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydrofuran (250 ml) containing 50 ml of methanol and 12.36 g (51.57 mmole) of N-cyano-3-amino-5-dimethylamino-6-chloropyrazinecarboxamidine is added hydroxylamine hydrochloride (6.65 g, 103.13 mmole) and triethylamine (21.56 ml, 154.71 mmole). The resulting reaction mixture is protected from moisture (calcium chloride) and heated to reflux for 6 hours. The reaction mixture is cooled, poured into water (1 l) and the yellow solid which forms is collected by filtration. Concentration of the filtrate affords more solid which when combined with the first crop yields 12.64 g (96%) of the desired product. The reaction product is dried at 60° C. and directly affords analytically pure 3-amino-5-[3-amino-5-dimethylamino-6-chloropyrazin-2-yl]-1,2,4-oxadiazole, m.p. 210°-211° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureto reflux for 6 hours
  4. temperatureThe reaction mixture is cooled
  5. filtrationthe yellow solid which forms is collected by filtration
  6. customConcentration of the filtrate affords more solid which when

Sources & evidence

ORD record
ord-81619c79dba441bbb28ec885ea6c502d
Source dataset
uspto-grants-1982_12
Patent number
US04362724

Reaction notes

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