Choline → HCID 20228194, compound

HRID 1731664Notes

Reaction equation

HRID 1731664 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1.C(O)C.[NH:15]([C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1)[NH2:16].OCC[N+](C)(C)C>CO>[NH2:9][C:8]1[CH2:7][CH:6]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[N:15]([C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[N:16]=1

Participants

6

Reactant 4

HCID 305CholineHCID 702EthanolHCID 119882-Benzothiazolinone, hydrazoneHCID 342433-(4-Chlorophenyl)prop-2-enenitrile

Product 1

HCID 20228194HCID 20228194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.28 g. of p-chlorocinnamonitrile, 50 ml. of absolute ethanol, 3.1 g. of 2-hydrazinobenzothiazole and 1.0 g. of 50% w/v choline in methanol is refluxed on a steam bath for 16 hours. The reaction mixture is cooled and the precipitate is collected by filtration. The solid is washed with ethanol to yield 3.2 g. of crude product. This material is recrystallized from acetone to give 1.65 g. of the product of the Example as yellow crystals, m.p. 273°-275° C.

Workup

  1. additionA mixture of 3.28 g
  2. temperatureis refluxed on a steam bath for 16 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitate is collected by filtration
  5. washThe solid is washed with ethanol
  6. customto yield 3.2 g
  7. customThis material is recrystallized from acetone
  8. customto give 1.65 g

Sources & evidence

ORD record
ord-62d8c26c1b16452c80315d7125bb472f
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

Loading…