N-Methylaniline → HCID 54153957, compound

HRID 1939833Notes

Reaction equation

HRID 1939833 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:15]2[CH2:17][O:16]2)[CH2:10][C:11]([O:13]C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>FC(F)(F)CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:17][N:19]([CH3:18])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:16][C:11](=[O:13])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 18936595HCID 18936595, compound

Product 1

HCID 54153957HCID 54153957, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Conditions

Temperature
23 °C

Procedure

Treat a solution of the product of step 2 (368 mg, 1.34 mmol) in 2,2,2 trifluoroethanol (1 mL) with N-methyl aniline (217 μL, 2.01 mmol, 1.5 eq) and stir for 6 h at 23° C. followed by 6 h at 80° C. Cool to 23° C., concentrate in vacuo and purify by silica gel chromatography (column: 3.5×12 cm; eluant: hexane:EtOAc (4:1)) to provide 446 mg (1.3 mmol, 97%) of 4-(3,4-dichlorophenyl)-dihydro-5-[(methylphenylamino)methyl]-2(3H)furanone as a white solid.

Workup

  1. waitfollowed by 6 h at 80° C
  2. temperatureCool to 23° C.
  3. concentrationconcentrate in vacuo
  4. custompurify by silica gel chromatography (column: 3.5×12 cm; eluant: hexane:EtOAc (4:1))

Sources & evidence

ORD record
ord-5a765cf1162c41aa995256f1e87fa546
Source dataset
uspto-grants-1997_12
Patent number
US05696267

Reaction notes

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