Diazald → Diazomethane

HRID 1685064Notes

Reaction equation

HRID 1685064 reaction equation
[CH3:1]C1C=CC(S([N:11]([N:13]=O)[CH3:12])(=O)=O)=CC=1.[OH-].[K+].[N+:17](=[CH2:19])=[N-:18].[CH3:20][C:21]1[CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]=1C>C(OCCOCCO)C.CCOCC.C(O)(=O)C>[N+:11](=[CH2:12])=[N-:13].[CH3:1][C:19]12[CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:21]1([CH3:23])[CH2:20][N:18]=[N:17]2

Participants

9

Reactant 4

HCID 6628DiazaldHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 12403518Ethyl 2,3-dimethylcycloprop-2-ene-1-carboxylate

Product 2

HCID 9550DiazomethaneHCID 58055077HCID 58055077, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8146Diethylene Glycol Monoethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Diazomethane was prepared from Diazald (21.5 g), KOH (6.6 g) in 2-(2-ethoxyethoxy)ethanol (35 mL). To the diazomethane solution in Et2O was added ethyl 2,3-dimethylcycloprop-2-enecarboxylate as obtained above. The mixture was stirred at 0° C. for 14 days in the dark. A solution of acetic acid in Et2O was added to quench off remaining diazomethane and the volatiles were removed in vacuo. Remaining starting material was removed by Kugelrohr distillation to afford ethyl 1,5-dimethyl-2,3-diaza-bicyclo[3.1.0]hex-2-ene-6-carboxylate (1.25 g, 6.9 mmol) as a yellowish oil in 10% yield over 2 steps.

Workup

  1. customas obtained above
  2. customto quench off
  3. customthe volatiles were removed in vacuo
  4. customwas removed by Kugelrohr distillation

Sources & evidence

ORD record
ord-85b86ee534a34795aa7a819c301cbbda
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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