N,N-Diethylethylenediamine → HCID 20096997, compound

HRID 1769594Notes

Reaction equation

HRID 1769594 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5](OC)[C:6]2[C:7](=[N:9][O:10][N+:11]=2[O-:12])[N:8]=1.[CH2:15]([N:17]([CH2:20][CH2:21][NH2:22])[CH2:18][CH3:19])[CH3:16]>CO>[CH2:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH2:21][NH:22][C:5]1[C:6]2[C:7](=[N:9][O:10][N+:11]=2[O-:12])[N:8]=[C:3]([O:2][CH3:1])[N:4]=1)[CH3:16]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 12288984HCID 12288984, compound

Product 1

HCID 20096997HCID 20096997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.0 g (15 mmol) of 5,7-dimethoxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide (J. Chem. Soc. Perkin Trans. 1, 1976, 1327), 1.75 g (15 mmol) of diethylaminoethylamine and 120 ml of methanol is stirred at room temperature for 2 hours and then concentrated in a rotary evaporator. The residue is dissolved hot in isopropanol, and the solution is filtered and treated with the same amount of hot petroleum ether. Overnight, 2.5 g (59%) of 7-(2-diethylaminoethylamino)-5-methoxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide crystallise out.

Workup

  1. concentrationconcentrated in a rotary evaporator
  2. dissolutionThe residue is dissolved hot in isopropanol
  3. filtrationthe solution is filtered
  4. additiontreated with the same amount of hot petroleum ether
  5. customOvernight, 2.5 g (59%) of 7-(2-diethylaminoethylamino)-5-methoxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide crystallise out

Sources & evidence

ORD record
ord-b4ead746abd4405b8711b9623310acd2
Source dataset
uspto-grants-1995_01
Patent number
US05382585

Reaction notes

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