Hydrochloric Acid → HCID 14722307, compound

HRID 1031672Notes

Reaction equation

HRID 1031672 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14].[H-].[Na+].[C:24]([O:28][CH3:29])(=[O:27])[C:25]#[CH:26].Cl>CN(C)C=O.C(OCC)(=O)C.O>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]/[CH:26]=[CH:25]/[C:24]([O:28][CH3:29])=[O:27])=[CH:7][C:6]=1[NH:12][S:13]([CH3:16])(=[O:14])=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 13536Methyl propiolateHCID 24758Sodium hydrideHCID 14722268HCID 14722268, compound

Product 1

HCID 14722307HCID 14722307, compoundYield 31.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22.5 °C

Procedure

3 g of 4-(2,4-difluorophenoxy)-3-methylsulfonylaminophenol was dissolved in 15 ml of N,N-dimethylformamide. 420 mg of sodium hydride (purity: 60%) was added. The mixture was stirred for 20 minutes at 20-25° C. Then, 0.88 g of methyl propiolate was added dropwise in about 5 minutes so that the reaction temperature was maintained below 40° C. The mixture was stirred for 30 minutes at 30°-40° C. After the completion of the reaction, 50 ml of water and 50 ml of ethyl acetate were added thereto. The resulting mixture was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (eluant: a 20:1 mixture of toluene and ethyl acetate) to obtain 1.2 g (yield: 31.6%) of methyl trans-3-[4-(2,4-difluorophenoxy)-3-methylsulfonylaminophenoxy]acrylate.

Workup

  1. temperaturewas maintained below 40° C
  2. stirringThe mixture was stirred for 30 minutes at 30°-40° C
  3. additionwere added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by a column chromatography (eluant
  9. additiona 20:1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-78d17bccbe5f4f46a3052a45ab325c11
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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