Formic Acid → HCID 9862983, compound

HRID 1532277Notes

Reaction equation

HRID 1532277 reaction equation
[Br: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>[Br: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]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 212517343-Bromo-4-(methanesulfonyl)benzaldehyde

Product 1

HCID 9862983HCID 9862983, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution containing 0.68 g 3-bromo-4-methylsulfonylbenzaldehyde, 0.03 ml piperidine and 0.02 ml formic acid in 20 ml DMF was added 0.59 ml 2,4-pentanedione with stirring at 20° C. The solution was stirred overnight at 20° C. and poured into water. The product was extracted with ethyl acetate, washed with water and evaporated to dryness in vacuo. The residue was crystallized from methanol, yield 0.18 g (20%), mp 135-139° C. 1H-NMR (DMSO-d6, 400 MHz): 2.28 (s, 3 H, CH3), 2.50 (s, 3 H, CH3), 3.36 (s, 3 H, CH3), 7.60 (d, 1 H, Ar), 7.99 (d, 1 H, Ar), 8.12 (d, 1 H, Ar), 7.71 (s, 1 H, CH).

Workup

  1. stirringThe solution was stirred overnight at 20° C.
  2. extractionThe product was extracted with ethyl acetate
  3. washwashed with water
  4. customevaporated to dryness in vacuo
  5. customThe residue was crystallized from methanol, yield 0.18 g (20%), mp 135-139° C

Sources & evidence

ORD record
ord-f6d931d0fe384b5c8333757cce401247
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

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