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Formic Acid → 3-{[3-Chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

HRID 1532275
Notes
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Reaction equation

HRID 1532275 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=O.N1CCCCC1.C(O)=O.[CH3:23][C:24](=[O:29])[CH2:25][C:26](=[O:28])[CH3:27]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:25]([C:24](=[O:29])[CH3:23])[C:26](=[O:28])[CH3:27])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 117361153-Chloro-4-methanesulfonyl-benzaldehyde

Product 1

HCID 98178223-{[3-Chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution containing 1.42 g 3-chloro-4-methylsulfonylbenzaldehyde, 0.05 ml piperidine and 0.02 ml formic acid in 20 ml DMF was added 1.50 ml 2,4-pentanedione with stirring at 20° C. The solution was stirred overnight at 20° C. and poured into water. The oily residue was separated and crystallized from ethanol, yield 0.24 g (10%), mp. 140-142° C. 1H-NMR (DMSO-d6, 400 MHz): 2.28 (s, 3 H, CH3), 2.50 (s, 3 H, CH3), 3.40 (s, 3 H, CH3), 7.60 (m, 1 H, Ar), 7.80 (m, 1 H, Ar), 7.77 (s, 1 H, CH), 8.1 (m, 1 H, Ar).

Workup

  1. stirringThe solution was stirred overnight at 20° C.
  2. customThe oily residue was separated
  3. customcrystallized from ethanol, yield 0.24 g (10%), mp. 140-142° C

Sources & evidence

ORD record
ord-de339383eb1d462a9d3663ea43e390d7
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06201027B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes