4-Nitrobenzoyl chloride → Ethanone,2-diazo-(4-nitrophenyl)-

HRID 1588047Notes

Reaction equation

HRID 1588047 reaction equation
[N+:1](=[CH2:3])=[N-:2].CN(N=O)/C(/N)=N/[N+]([O-])=O.[OH-].[K+].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>CCOCC>[N+:1](=[CH:3][C:23]([C:22]1[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=1)=[O:24])=[N-:2]

Participants

6

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 95620601-Methyl-2-nitro-1-nitrosoguanidine

Product 1

HCID 138152Ethanone,2-diazo-(4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The ethereal diazomethane solution [prepared by adding 12.5 g n-methyl-n-nitro-n-nitroso guanidine to potassium hydroxide (50%, 20 ml) and ether (200 ml) at 0°, stirring for 1 hr, and decanting the ether layer; 65% presumed yield] is treated with TEA (7.7 ml) at 0°, then dropwise with p-nitrobenzoyl chloride (10.21 ml) in ether (25 ml). After stirring for 19 hrs, the reaction is filtered through celite and concentrated to give the title compound.

Workup

  1. customdecanting the ether layer
  2. custom65% presumed yield]
  3. stirringAfter stirring for 19 hrs
  4. filtrationthe reaction is filtered through celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec9c738cda3543fe863edba5cb923f72
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

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