Dimethylacetamide → HCID 131722381, compound

HRID 843515Notes

Reaction equation

HRID 843515 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[S:12]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)([OH:15])(=[O:14])=[O:13].[OH:23][O:24][O:25][O:26][O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[C:40]1(=[O:50])[NH:44][C:43](=[O:45])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12.[K].[CH3:52][C:53]([N:55]([CH3:57])C)=[O:54]>>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[S:12]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)([OH:15])(=[O:14])=[O:13].[C:40]1(=[O:50])[N:44]([C:28]([N:55]2[C:53](=[O:54])[C:52]3=[CH:7][CH:6]=[CH:5][CH:11]=[C:10]3[C:57]2=[O:13])([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[O:27][O:26][O:25][O:24][OH:23])[C:43](=[O:45])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 24194345Phthalimide potassium saltHCID 86757981HCID 86757981, compound

Product 1

HCID 131722381HCID 131722381, compound

Conditions

Temperature
165 °C

Procedure

A suspension of ditosylate (Step 3; 108 g), potassium phthalimide (75 g) in dimethylacetamide (700 mL) is heated at 165° C. for 2 hrs with vigorous stirring. The reaction mixture is then cooled to room temperature and the precipitate filtered. The precipitate is washed with water and acetone to afford 53 g of the desired product as a white solid.

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. filtrationthe precipitate filtered
  3. washThe precipitate is washed with water and acetone

Sources & evidence

ORD record
ord-772b8588e09148839dbef1b325d49fe6
Source dataset
uspto-grants-2002_04
Patent number
US06379930B1

Reaction notes

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