1,4-Dioxane → HCID 58542350, compound

HRID 1951900Notes

Reaction equation

HRID 1951900 reaction equation
O1CCOCC1.C(OC(=O)[NH:13][C:14]([C:26]1[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=1)([CH3:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=1)=[O:16])(C)(C)C.Cl.O1CCOCC1>O>[NH2:13][C:14]([C:26]1[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=1)([CH3:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 204431481,4-Dioxane hydrochlorideHCID 58542326HCID 58542326, compound

Product 1

HCID 58542350HCID 58542350, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dioxane (1 ml) solution of the compound (1.23 g, 2.55 mmol) obtained in Step 5 above was added to a 4 N hydrochloric acid/dioxane solution (5 ml) under ice cooling and the resulting mixture was gradually warmed and stirred at room temperature for 2 hours. The reaction mixture was diluted with water and washed with an n-hexane/ethyl acetate mixed solvent and then the aqueous layer was made alkaline by the addition of 15% aqueous sodium hydroxide solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:1 (v/v)] to give the title compound (0.75 g, 95%) as a pale yellow solid.

Workup

  1. temperaturethe resulting mixture was gradually warmed
  2. washwashed with an n-hexane/ethyl acetate mixed solvent
  3. additionby the addition of 15% aqueous sodium hydroxide solution
  4. extractionfollowed by extraction with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=1:1 (v/v)]

Sources & evidence

ORD record
ord-b5fc96b73d844b11b3069f22a98ac57b
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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