N'-Benzylidene-4-methylbenzene-1-sulfonohydrazide → Benzene, (diazomethyl)-

HRID 1954755Notes

Reaction equation

HRID 1954755 reaction equation
S([NH:11][N:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[C:14]1([CH:13]=[N+:12]=[N-:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 277551N'-Benzylidene-4-methylbenzene-1-sulfonohydrazideHCID 10942334Sodium Methoxide

Product 1

HCID 136601Benzene, (diazomethyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an oven-dried round bottom flask was placed benzaldehyde tosylhydrazone (1.15 g, 4.2 mmol), followed by 4.3 mL of a 1.0M solution of sodium methoxide in methanol (2.3 g Na metal dissolved in absolute methanol and diluted to 100 mL). The mixture was swirled until all the contents dissolved. Most of the solvent was removed via romy evaporation and the last traces of solvent by evacuation of the flask under high vacuum for 2 hours. The solid obtained was subjected to a Kugelrohr distillation at 215° C. and 200 millitorr for 1 hour. At 68-70° C., the title compound, as a red oil, was collected in a receiver flask in a quantitative yield.

Workup

  1. customIn an oven-dried round bottom flask was placed
  2. dissolutiondissolved
  3. customMost of the solvent was removed via romy evaporation
  4. customThe solid obtained
  5. distillationwas subjected to a Kugelrohr distillation at 215° C.
  6. wait200 millitorr for 1 hour
  7. customAt 68-70° C., the title compound, as a red oil, was collected in a receiver flask in a quantitative yield

Sources & evidence

ORD record
ord-85a84420acbd433fa7065761804ed02b
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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