Sodium Hydroxide → HCID 11350681, compound

HRID 2216254Notes

Reaction equation

HRID 2216254 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:23])[CH2:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:15]=2)[CH:11]=1.[CH2:25]([O:27][CH2:28]Cl)[CH3:26].[OH-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:24])=[N:4][S:5][C:6]=1[N:7]([CH2:28][O:27][CH2:25][CH3:26])[C:8](=[O:23])[CH2:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:15]=2)[CH:11]=1.[CH2:25]([O:27][CH2:28][N:4]1[CH:3]([CH3:24])[CH:2]([Cl:1])[C:6](=[N:7][C:8](=[O:23])[CH2:9][C:10]2[CH:18]=[CH:17][C:16]3[C:12](=[CH:13][N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:15]=3)[CH:11]=2)[S:5]1)[CH3:26]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 18523Chloromethyl ethyl etherHCID 11360470HCID 11360470, compound

Product 2

HCID 11350681HCID 11350681, compoundHCID 69667892HCID 69667892, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (0.50 g, 0.0014 mol) was dissolved in dichloromethane (15 ml) and the solution was cooled to 5° C. Chloromethyl ethyl ether (0.32 ml, 0.0035 mol), 50% aqueous sodium hydroxide solution (0.56 ml) and benzyltriethylammonium chloride (0.018 g) were added sequentially and then the mixture was stirred for 2 hours. The mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, initially eluting with 3:1 diethyl ether:hexane, then with diethyl ether and finally with ethyl acetate to give N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (0.16 g) as a yellow oil and N-[2-ethoxymethyl-4-chloro-3-methylisothiazolin-5-ylidene]-[2-(2-methylpropyl)indazol-5-yl) acetamide (0.20 g) as a cream-coloured solid (m.p. 105–106° C.).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washinitially eluting with 3:1 diethyl ether

Sources & evidence

ORD record
ord-aa1bdfb9ad7c4acfb7808f9b4edad3e4
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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