Choline → HCID 20228186, compound

HRID 1731663Notes

Reaction equation

HRID 1731663 reaction equation
[C:1](#[N:5])/[CH:2]=[CH:3]/[CH3:4].[NH:6]([C:8]1[S:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1)[NH2:7].OCC[N+](C)(C)C>C(O)C>[NH2:5][C:1]1[CH2:2][CH:3]([CH3:4])[N:6]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 305CholineHCID 119882-Benzothiazolinone, hydrazoneHCID 637921Crotononitrile

Product 1

HCID 20228186HCID 20228186, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20.1 g. of crotononitrile, 80 ml. of absolute ethanol, 4.87 g. of 2-hydrazinobenzothiazole and 1.5 ml. of 50% methanolic choline is refluxed for 16 hours. The solvent is removed in vacuo and water is added. The separated solid is collected by filtration, dissolved in dichloromethane, and passed through a short column of hydrous magnesium silicate. The effluent is refluxed with the gradual addition of hexane to give a crystalline product. The crystallization step is repeated to give 0.5 g. of the product of the Example as off-white plates, m.p. 212°-215° C.

Workup

  1. additionA mixture of 20.1 g
  2. customThe solvent is removed in vacuo and water
  3. additionis added
  4. filtrationThe separated solid is collected by filtration
  5. dissolutiondissolved in dichloromethane
  6. temperatureThe effluent is refluxed with the gradual addition of hexane
  7. customto give a crystalline product
  8. customThe crystallization step
  9. customto give 0.5 g

Sources & evidence

ORD record
ord-f8e127535d1b4b35b6646bf792d8bbc1
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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