p-Toluenesulfonic acid → HCID 178517978, compound

HRID 2106566Notes

Reaction equation

HRID 2106566 reaction equation
[C:1]1([NH:7][NH:8][C:9]([NH2:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[OH:10][C:9]1[N:11]=[CH:12][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 61002Phenicarbazide

Product 1

HCID 178517978HCID 178517978, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

One hundred g of 1-phenylsemicarbazide was added to 500 ml of trimethyl orthoformate, and about 400 mg of p-toluenesulfonic acid was added to the mixture. It was heated on a steam bath with strong agitation for 2 hours, and was then transferred to a large flask, cooled and evaporated under vacuum. The residue was recrystallized from about 1600 ml of acetic acid to obtain 97 g of the desired intermediate, m.p. 277°-280°.

Workup

  1. additionwas added to the mixture
  2. temperatureIt was heated on a steam bath with strong agitation for 2 hours
  3. customwas then transferred to a large flask
  4. temperaturecooled
  5. customevaporated under vacuum
  6. customThe residue was recrystallized from about 1600 ml of acetic acid

Sources & evidence

ORD record
ord-c6076c06fe7e42d0bcefc3b8cff2bf6f
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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