Diazomethane → Diazomethane

HRID 1588046Notes

Reaction equation

HRID 1588046 reaction equation
[CH3:1][N:2]([N:9]=O)C(N[N+]([O-])=O)=N.[OH-].[K+].[N+:13](=[CH2:15])=[N-:14].[CH:16]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCOCC>[N+:2](=[CH2:1])=[N-:9].[CH:16]1([C:22](=[O:23])[CH:15]=[N+:13]=[N-:14])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Product 2

HCID 9550DiazomethaneHCID 53903884HCID 53903884, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane is prepared from N-methyl-N'-nitro-N-nitroso guanidine (12.5 g), potassium hydroxide (50%, 20 ml), and ether (300 ml). TEA (7.7 ml) is added to the diazomethane solution (65%) followed by cyclohexane carboxylic acid chloride (7.4 ml) slowly at 0° . The reaction is stirred at 0° for 1 hr then for 18 hrs at 22° . A porecipitate forms, it is filtered and washed with ether, and the filtrate concentrated. The resulting oil is cooled to -78° , triturated with ether, then warmed to 22° and concentrated with reduced pressure and heat to give the title compound as an oil, NMR (acetone-d6) 5.4 and 1.4-0.8 δ.

Workup

  1. waitfor 18 hrs at 22°
  2. filtrationA porecipitate forms, it is filtered
  3. washwashed with ether
  4. concentrationthe filtrate concentrated
  5. temperatureThe resulting oil is cooled to -78°
  6. customtriturated with ether
  7. temperaturewarmed to 22°
  8. concentrationconcentrated with reduced pressure
  9. temperatureheat

Sources & evidence

ORD record
ord-511508def6a047a6bd8e2f60f8f13887
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

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