2,4-Dichlorobenzyl chloride → HCID 58109404, compound

HRID 2037590Notes

Reaction equation

HRID 2037590 reaction equation
[CH2:1]([C:4]1([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[O:9][C:8](=[O:10])[NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21]Cl.[H-].[Na+]>CN(C=O)C>[CH2:1]([C:4]1([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[O:9][C:8](=[O:10])[N:7]([CH2:21][C:20]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:19]=2[Cl:18])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 58109248HCID 58109248, compound

Product 1

HCID 58109404HCID 58109404, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-allyl-6-(4-fluorophenyl)-1,3-oxazinan-2-one (15 mg, 0.064 mmol) and 2,4-dichlorobenzyl chloride (25 mg, 0.13 mmol) in dry DMF (0.5 mL) under N2 was added 60% NaH in oil in small portions until gas evolution ceased. The mixture was stirred overnight at rt and quenched with water (0.5 mL). The mixture was applied to a 10-mL Chem-Elut cartridge and eluted with ether (50 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford 6-allyl-3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (5.5 mg, 22%). LC-MS Method 1 tR=2.1 min, m/z=394; 1H NMR (CDCl3) 2.30 (2H), 2.60 (m, 2H), 2.96 (m, 1H), 3.08 (m, 1H), 4.44 (d, 1H), 4.65 (d, 1H), 4.75 (1H), 5.06 (m, 2H), 5.67 (m, 1H), 6.86 (d, 1H), 7.08 (3H), 7.30 (3H).

Workup

  1. customquenched with water (0.5 mL)
  2. washeluted with ether (50 mL)
  3. customThe eluate was evaporated to dryness
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5c885a59afab47bcae202bd7a5cb47ad
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…