Benzoyl chloride → Diazomethane

HRID 1588048Notes

Reaction equation

HRID 1588048 reaction equation
[CH3:1][N:2]([N:9]=O)/C(/N)=N/[N+]([O-])=O.C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[N+:2](=[CH2:1])=[N-:9].[N+:2](=[CH:1][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:25])=[N-:9]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 95620601-Methyl-2-nitro-1-nitrosoguanidine

Product 2

HCID 9550DiazomethaneHCID 18667Diazoacetophenone

Procedure

An ethereal solution of diazomethane is prepared from n-methyl-n-nitro-n-nitroso guanidine (15.72 g) for an estimated yield of 64 mmol. To the ethereal solution (400 ml) at 0° is added triethylamine (9.0 ml, 64 mmol), then dropwise benzoyl chloride (7.4 ml, 64 mmol). The reaction is warmed to 22° and stirred for 20 hrs, then filtered through celite and concentrated. The residue is recrystallized from ether/pentane to give the title compound.

Workup

  1. temperatureThe reaction is warmed to 22°
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe residue is recrystallized from ether/pentane

Sources & evidence

ORD record
ord-7538c669ae334f6eaba262652748a676
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

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