Acetophenone → HCID 68503997, compound

HRID 2387614Notes

Reaction equation

HRID 2387614 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[F:10][C:11]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:12]=1[C:13](=[S:16])[NH:14][NH2:15]>CCO.C(Cl)Cl>[F:10][C:11]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:12]=1[C:13]1[S:16][C:1]([CH3:2])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazide

Product 1

HCID 68503997HCID 68503997, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of acetophenone (0.600 g, 5.00 mmol) in 20 mL of a 3:1 EtOH/DCM mixture was added 2,5-difluorobenzothiohydrazide (0.941 g, 5.00 mmol). The reaction was allowed to stir overnight at room temperature. The reaction was then heated to 45° C., for 14 hours. The reaction mixture was then concentrated in vacuo, and the residue was loaded directly to Biotage (45), followed by flash column chromatography (20% ethyl acetate/hexanes), yielding 5-(2,5—the desired product (1.021 g, 70% yield) as a yellow semi-solid.

Workup

  1. temperatureThe reaction was then heated to 45° C., for 14 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-2c66f6bf98644d4488bcc46e8b35b88f
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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