Sodium hydride → HCID 86594268, compound

HRID 1182247Notes

Reaction equation

HRID 1182247 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][C:4]=1[S:11]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:16]=1[CH3:29])(=[O:13])=[O:12].[H-].[Na+].Cl.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]Cl.[O-][Si]([O-])=O.[Mg+2]>CN(C=O)C>[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][N:14]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:16]=1[CH3:29])[S:11]([C:4]1[CH:5]=[C:6]([CH3:10])[CH:7]=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 61680MAGNESIUM SILICATE (synthetic)HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 86594269HCID 86594269, compound

Product 1

HCID 86594268HCID 86594268, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 32 (103 mg, 0.25 mmol) in anhydrous DMF (5 mL) was added NaH (60% dispersion in mineral oil, 22 mg, 0.54 mmol). The mixture was stirred for 10 min at room temperature before the addition of 2-(dimethylamino)-ethyl chloride hydrochloride (39.2 mg, 0.27 mmol). The resulting mixture was heated overnight at 85° C. After a usual workup, the residue was loaded onto column (Florisil) and the column eluted with EtOAc/CH3OH (10:1) to give 80 mg of the title compound as an off-white solid. ESI [M+H+]=488.27.

Workup

  1. washthe column eluted with EtOAc/CH3OH (10:1)

Sources & evidence

ORD record
ord-5c938f5a0671465fac8fd7619805946a
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

Loading…