Dichloromethane → HCID 67816532, compound

HRID 2401437Notes

Reaction equation

HRID 2401437 reaction equation
C([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[C:7]=1[C:12]1[C:13]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[N:14][N:15]([CH3:17])[CH:16]=1)(=O)C.[OH-].[Na+].C(Cl)Cl>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:13]2[C:12]([C:7]3[C:8]([CH3:11])=[N:9][O:10][C:6]=3[CH2:5][OH:4])=[CH:16][N:15]([CH3:17])[N:14]=2)=[O:26])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67816276HCID 67816276, compound

Product 1

HCID 67816532HCID 67816532, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (4-(3-(4-chlorobenzoyl)-1-methyl-1H-pyrazol-4-yl)-3-methylisoxazol-5-yl)methyl acetate (0.3 g, 0.8 mmol) in THF (10 mL), was added NaOH solution (5 mL, 1 N in water). The mixture was stirred for 2 hours at 55° C. After cooling to room temperature, DCM (50 mL) was added and the layers separated. The separated organic layer was dried over anhydrous sodium sulfate and concentrated to afford the titled product as a yellow oil (0.2 g, 75% yield). LC/MS m/z 331 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.13 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 3H), 4.62 (s, 2H), 4.07 (s, 3H), 2.15 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe layers separated
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b14c3ba75a08457f898bb8034363c95d
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…