Acetic Acid → 6-ethyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxide

HRID 1769595Notes

Reaction equation

HRID 1769595 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([N+:10]([O-:12])=[O:11])=[C:6]2[NH:13]N=N[N:5]2[C:4]1=[O:16])[CH3:2].C(O)(=O)C>C1(C)C(C)=CC=CC=1>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2=[N+:10]([O-:12])[O:11][N:13]=[C:6]2[NH:5][C:4]1=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1784629686-ethyl-8-nitrotetrazolo[1,5-c]pyrimidine-5,7(1H,6H)-dione

Product 1

HCID 1357956596-ethyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxideYield 77%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

20.0 g of 6-ethyl-8-nitrotetrazolo[1,5-c]pyrimidine-5,7(1H,6H)-dione are heated at 120° C. for 7 hours with 200 ml of glacial acetic acid in 2000 ml of xylene. A small undissolved portion is filtered off, the filtrate is concentrated in vacuo and the oily residue is made to crystallise by trituration with methylene chloride. 13.5 g (77%) of 6-ethyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxide are obtained.

Workup

  1. filtrationA small undissolved portion is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto crystallise by trituration with methylene chloride

Sources & evidence

ORD record
ord-e5caf30b569e4eda9af60ec0c493525d
Source dataset
uspto-grants-1995_01
Patent number
US05382585

Reaction notes

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