Water → HCID 22719958, compound

HRID 1582194Notes

Reaction equation

HRID 1582194 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.Cl[CH2:10][C:11]([N:13]([C:15]1[C:16](=[O:31])[C:17]2[C:22]([C:23](=[O:30])[C:24]=1[NH:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:14])=[O:12].O>O1CCCC1>[CH3:29][O:28][CH2:27][CH2:26][NH:25][C:24]1[C:23](=[O:30])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:31])[C:15]=1[N:13]([CH3:14])[C:11](=[O:12])[CH2:10][N:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 22320367Dimethylamine tetrahydrofuranHCID 22719978HCID 22719978, compound

Product 1

HCID 22719958HCID 22719958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M Dimethylamine/tetrahydrofuran solution (3.0 ml) was added to a solution of 2-chloro-N-[1,4-dihydro-3-(2-methoxyethyl)amino-1,4-dioxo-2-naphthalenyl]-N-methylacetamide (0.5 g) in tetrahydrofuran (30 ml) and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from ethanol to give N-[1,4-dihydro-3-(2-methoxyethyl)amino-1,4-dioxo-2-naphthalenyl]-N-methyl-2-(dimethylamino)acetamide (0.19 g) as a brown powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-c75c3b25e0ea4c23a05a3e2536ffc2fd
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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