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

HRID 1532289Notes

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]>CC(O)C>[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]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution containing 2.5 g of 3-chloro-4-methylsulfonylbenzaldehyde, 0.13 ml of piperidine and 0.05 ml of formic acid in 70 ml of 2-propanol was added 2.6 ml of 2,4-pentanedione with stirring at 20° C. The solution was stirred overnight at 20° C. The product was filtrated and washed with 2-propanol, yield 2.1 g (60%), 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

stirringThe solution was stirred overnight at 20° C
filtrationThe product was filtrated
washwashed with 2-propanol, yield 2.1 g (60%), mp. 140-142° C

Sources & evidence

ORD record: ord-6c70006b655145ea909d8f6a34535000
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201027B1

Reaction notes

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