Potassium Hydroxide → 3-Methoxyethoxyethoxyethylnaphtho[2,1-d]thiazolin-2-on

HRID 1449590Notes

Reaction equation

HRID 1449590 reaction equation
[S:1]1[C:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]=2[NH:3][C:2]1=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH:23](I)[CH3:24].[OH-].[K+]>C(O)C>[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][N:3]1[C:4]2[CH:13]=[CH:12][C:11]3[C:6]([C:5]=2[S:1][C:2]1=[O:14])=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 6398532Naphtho[2,1-d]thiazol-2(3H)-oneHCID 233521122-Methoxyethoxyethoxy-1-iodoethane

Product 1

HCID 572725413-Methoxyethoxyethoxyethylnaphtho[2,1-d]thiazolin-2-on

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g of naphtho[2,1-d]thiazoline-2-on, 3.0 g of 2-methoxyethoxyethoxy-1-iodoethane (synthesized from methoxyethoxyethoxyethyl p-toluenesulfonate and sodium iodide), 0.6 g of potassium hydroxide and 20 ml of ethanol were fed into a 50 ml short-neck flask provided with a reflux condenser, and heated under reflux and under stirring for 4 hours. After cooling to room temperature followed by extraction with 300 ml of ethyl acetate and 150 ml of water, the thus-obtained ethyl acetate layer was dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained compound was purified by column chromatography (hexane:ethyl acetate=1:1) to obtain the intended compound.

Workup

  1. customprovided with a reflux condenser
  2. temperatureheated
  3. temperatureunder reflux
  4. extractionfollowed by extraction with 300 ml of ethyl acetate and 150 ml of water
  5. dry with materialthe thus-obtained ethyl acetate layer was dried over sodium sulfate, and ethyl acetate
  6. distillationwas distilled off under reduced pressure
  7. customThe obtained compound was purified by column chromatography (hexane:ethyl acetate=1:1)
  8. customto obtain the intended compound

Sources & evidence

ORD record
ord-1985b93f7dc447d982a26cd2472f41f9
Source dataset
uspto-grants-1997_02
Patent number
US05599825

Reaction notes

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