Ciclopirox → HCID 54760963, compound

HRID 919114Notes

Reaction equation

HRID 919114 reaction equation
[CH:1]1([C:7]2[N:12]([OH:13])[C:11](=[O:14])[CH:10]=[C:9]([CH3:15])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16]1([C:22](Cl)=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:22]([O:13][N:12]1[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:8][C:9]([CH3:15])=[CH:10][C:11]1=[O:14])(=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 2749CiclopiroxHCID 7412Benzoyl chloride

Product 1

HCID 54760963HCID 54760963, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
7 °C

Procedure

To 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one (0.5 g) in CH2Cl2 (20 mL) were added DMAP (0.44 g) and PhCOCl (0.5 mL) at 7° C. After the mixture was stirred at 7° C. for 90 min, solvent was partially removed in vacuum. Water (20 mL) and ethyl acetate (20 mL) were added. The organic layer was collected and concentrated. The desired compound was recrystallized from ethyl acetate and petroleum ether to yield compound 338 (0.22 g).

Workup

  1. customsolvent was partially removed in vacuum
  2. additionWater (20 mL) and ethyl acetate (20 mL) were added
  3. customThe organic layer was collected
  4. concentrationconcentrated
  5. customThe desired compound was recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-7517e6413e6a43d9ba83584015c8cf42
Source dataset
uspto-grants-2016_03
Patent number
US09273005B2

Reaction notes

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