2-Benzothiazolinone, hydrazone → HCID 20228192, compound

HRID 1731665Notes

Reaction equation

HRID 1731665 reaction equation
[Na].[NH:2]([C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[NH2:3].[C:13](#[N:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[NH2:22][C:13]1[CH2:14][CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:2]([C:4]2[S:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[N:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 119882-Benzothiazolinone, hydrazoneHCID 746673-Phenylprop-2-enenitrileHCID 5360545Sodium

Product 1

HCID 20228192HCID 20228192, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.46 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 16.5 g. of 2-hydrazinobenzothiazole is added, followed by 12.9 g. of cinnamonitrile. The reaction mixture is refluxed for 16 hours, then is cooled. Some of the solvent is removed in vacuo and the mixture is filtered. The precipitate is washed with hexane to give 25.67 g. of crude product. A 3.0 g. amount of this material is recrystallized from acetone-hexane to give 2.35 g. of the product of the Example as buff colored prisms, m.p. 270°-271.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. temperatureis cooled
  3. customSome of the solvent is removed in vacuo
  4. filtrationthe mixture is filtered
  5. washThe precipitate is washed with hexane
  6. customto give 25.67 g
  7. customamount of this material is recrystallized from acetone-hexane
  8. customto give 2.35 g

Sources & evidence

ORD record
ord-0d3b1b400b8e4875b6c80872ce7e9f52
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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