Choline → HCID 20228180, compound

HRID 1731661Notes

Reaction equation

HRID 1731661 reaction equation
C(O[CH2:4][CH2:5][C:6]#[N:7])C.C(O)C.[NH:11]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)[NH2:12].OCC[N+](C)(C)C>CO>[NH2:7][C:6]1[CH2:5][CH2:4][N:11]([C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[N:12]=1

Participants

6

Reactant 4

HCID 305CholineHCID 702EthanolHCID 119882-Benzothiazolinone, hydrazoneHCID 16501Propanenitrile, 3-ethoxy-

Product 1

HCID 20228180HCID 20228180, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.0 g. of β-ethoxypropionitrile, 100 ml. of absolute ethanol, 8.25 g. of 2-hydrazinobenzothiazole and 2.5 g. of 50% w/v choline in methanol is refluxed on a steam bath for 16 hours, then the solvent is removed in vacuo. Water is added and the solid is collected by filtration. The solid is recrystalized twice from ethanol to give 5.75 g. of the product of the Example as grey prisms, m.p. 231.5°-235° C.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureis refluxed on a steam bath for 16 hours
  3. customthe solvent is removed in vacuo
  4. additionWater is added
  5. filtrationthe solid is collected by filtration
  6. customThe solid is recrystalized twice from ethanol
  7. customto give 5.75 g

Sources & evidence

ORD record
ord-96eb4ec0f63c4844ba66b37c8d009237
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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