Dimethyl acetylenedicarboxylate → HCID 178499188, compound

HRID 366946Notes

Reaction equation

HRID 366946 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:11]([O:13][CH3:14])=[O:12])#[C:6][C:7]([O:9][CH3:10])=[O:8]>CN(C=O)C>[NH:1]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 33557Sodium Azide

Product 1

HCID 178499188HCID 178499188, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium azide (5.03 g, 77.39 mmol) in DMF (120 mL) was added dropwise at 0° C. over 30 min, a solution of dimethyl acetylene-dicarboxylate (10.0 g, 70.36 mmol) in DMF (100 mL). After 30 min the solvent was removed in vacuo at 30° C. to leave a light purple-brown solid. The solid was washed twice with ether and taken up in water (100 mL). The aqueous solution was acidified with conc. HCl to pH 2. The aqueous layer was first extracted with ether (100 mL) and then with chloroform (100 mL). The combined organic layers were evaporated to give a light red colored solid: 128-130° C. The solid was washed with hot hexane and crystallized from benzene: Yield 11.0 g (85%); 1H NMR (CDCl3) δ 4.00 (s, 6H), 11.87 (br s, 1H, NH).

Workup

  1. additionwas added dropwise at 0° C. over 30 min
  2. customAfter 30 min the solvent was removed in vacuo at 30° C.
  3. customto leave a light purple-brown solid
  4. washThe solid was washed twice with ether
  5. extractionThe aqueous layer was first extracted with ether (100 mL)
  6. customThe combined organic layers were evaporated
  7. customto give a light red colored solid
  8. custom128-130° C
  9. washThe solid was washed with hot hexane
  10. customcrystallized from benzene

Sources & evidence

ORD record
ord-58879e66cd604d2390a84c394b49875a
Source dataset
uspto-grants-2000_10
Patent number
US06130326

Reaction notes

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