Hydrazinecarboxaldehyde → 3-methylbenzothiazol-2(3H)-one hydrazone

HRID 224682

Reaction equation

HRID 224682 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:12][N+:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15][C:14]=1SC.C([NH:26][NH2:27])=O>O>[CH3:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15][C:14]1=[N:26][NH2:27]

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 143193-methylbenzothiazol-2(3H)-one hydrazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a flask equipped with a reflux condenser and magnetic stirrer is charged 50 ml water. Then 28.1 g (0.076 moles) 3-methyl-2-methylthiobenzothiazolium p-toluene sulfonate is dissolved with slight heating. A solution of 9.1 g (0.15 moles) formylhydrazine in 25 ml of water then is added and the mixture is heated at reflux for 15 minutes. The cooled suspension is made acidic until a clear solution results, then made basic. The product precipitates and is filtered, giving 9.1 g (66%), m.p. 134° C.

Workup

  1. customInto a flask equipped with a reflux condenser and magnetic stirrer
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 15 minutes
  4. customresults
  5. customThe product precipitates
  6. filtrationis filtered
  7. customgiving 9.1 g (66%), m.p. 134° C.

Sources & evidence

ORD record
ord-ddf6340fa1db41a3aaf7dccd81bf8f7c
Source dataset
uspto-grants-1980_11
Patent number
US04233442

Linked notes

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