2-(Dimethylamino)ethanol → HCID 58503953, compound

HRID 2407782Notes

Reaction equation

HRID 2407782 reaction equation
[O:1]=[C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[C:31](Cl)(=[O:35])[C:32](Cl)=[O:33].[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][OH:41]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][O:41][C:31](=[O:35])[C:32]([N:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:2](=[O:1])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:7][CH2:6]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 65578Oxalyl chlorideHCID 58504041HCID 58504041, compound

Product 1

HCID 58503953HCID 58503953, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound prepared in Example 303 (100 mg) in toluene (20 mL) was treated with oxalyl chloride (0.09 mL) for 2 hours at room temperature. 2-(dimethylamino)ethanol (873 mg) was added and the reaction was stirred for 1 hour at room temperature. The solution was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title material (120 mg), which was used without further purification.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1946b44317c84c2592ae387bc46fa629
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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