Oxalic Acid → HCID 59366927, compound

HRID 1923981Notes

Reaction equation

HRID 1923981 reaction equation
[N+:1]([O-:4])([O-])=O.[Na+].C(O)(=O)C(O)=O.[N:12]([CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:20]=[N+:21]=[N-:22])=[N+:13]=[N-:14].CCCCCC>C(Cl)Cl>[N:20]([CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:12]=[N+:13]=[N-:14])[N:1]=[O:4])=[N+:21]=[N-:22]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 8058HexaneHCID 24268Sodium NitrateHCID 12104057HCID 12104057, compound

Product 1

HCID 59366927HCID 59366927, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of sodium nitrate (13.4 g; 0.194 mol), oxalic acid (24.4 g; 0.194 mol) and N,N-bis(2-azidoethyl)amine LI (15 g; 0.097 mol) in DCM (300 mL) was stirred vigorously at r.t. for 2.5 h. Silica gel (20 g) and hexane (200 mL) was added to the reaction mixture and the resulting suspension was filtered. The solids were washed (1:1 hexane/DCM, 200 mL). The solvent was evaporated under reduced pressure to afford N,N-bis(2-azidoethyl)-N-nitrosoamine LII (15 g; 0.081 mol; 84% yield).

Workup

  1. filtrationthe resulting suspension was filtered
  2. washThe solids were washed (1:1 hexane/DCM, 200 mL)
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1fc5f08c18c6481fbe5f8aa5f6422892
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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