Ethanol → N-(3-Chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-N-(2-methoxyethyl)acetamide

HRID 1582181Notes

Reaction equation

HRID 1582181 reaction equation
[Cl:1][C:2]1[C:3](=[O:18])[C:4]2[C:9]([C:10](=[O:17])[C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:19]([OH:21])[CH3:20].C(OCC)(=O)C>S(=O)(=O)(O)O.C(OC(=O)C)(=O)C>[Cl:1][C:2]1[C:3](=[O:18])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:17])[C:11]=1[N:12]([CH2:13][CH2:14][O:15][CH3:16])[C:19](=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 2601782-Chloro-3-[(2-methoxyethyl)amino]naphthalene-1,4-dione

Product 1

HCID 12987498N-(3-Chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-N-(2-methoxyethyl)acetamide

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
45 °C

Procedure

A few drops of concentrated sulfuric acid was added to a solution of 2-chloro-3-[(2-methoxyethyl)amino]-1,4-naphthoquinone (33 g) in acetic anhydride (100 ml) and the mixture was stirred at 45° C. for 1 hour. By adding ethanol (100 ml) to the reaction solution, excess acetic anhydride was esterified. After cooling, ethyl acetate was added to the reaction solution and the mixture was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was crystallized from diethyl ether to give N-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-N-(2-methoxyethyl)acetamide (29 g) as a yellow powder.

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-9f3426ccfd674e80b3a8e364c8188f79
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

Loading…