4-Chloro-2-hydroxybenzaldehyde → HCID 23447547, compound

HRID 1840592Notes

Reaction equation

HRID 1840592 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH:17]=[CH2:18])(=[O:16])=[O:15])[CH2:10][C:9]2=[O:19])=[CH:5][CH:4]=1)#[N:2].[Cl:22][C:23]1[CH:24]=[C:25]([OH:31])[C:26](=[CH:29][CH:30]=1)[CH:27]=O.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]2[CH:27]=[C:17]([S:14]([N:11]3[CH2:12][CH2:13][N:8]([CH2:7][C:6]4[CH:20]=[CH:21][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[C:9](=[O:19])[CH2:10]3)(=[O:16])=[O:15])[CH2:18][O:31][C:25]=2[CH:24]=1

Participants

5

Reactant 3

HCID 5201014-Chloro-2-hydroxybenzaldehydeHCID 23447465HCID 23447465, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23447547HCID 23447547, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-(4-cyanobenzyl)-4-vinylsulfonyl-2-piperazinone (1.53 g) and 4-chlorosalicylaldehyde (0.94 g) in tert-butanol (20 ml) was added potassium tert-butoxide (187 mg), and the mixture was refluxed for 4 days. The reaction solution was concentrated under reduced pressure, and precipitated crystals were washed with acetone-ethanol to give pale brown crystals of the title compound (0.88 g).

Workup

  1. temperaturethe mixture was refluxed for 4 days
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customprecipitated crystals
  4. washwere washed with acetone-ethanol

Sources & evidence

ORD record
ord-142108e70a5542e4bb31733f99eea057
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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