Ciclopirox → HCID 54760963, compound

HRID 2194626Notes

Reaction equation

HRID 2194626 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 petrelum 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 petrelum ether

Sources & evidence

ORD record
ord-adf59e67c9324f10b269e7dd607015b3
Source dataset
uspto-grants-2012_12
Patent number
US08334307B2

Reaction notes

Loading…