Ammonium Chloride → HCID 68450007, compound

HRID 511822Notes

Reaction equation

HRID 511822 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9](/[CH:12]=[N:13]/[S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[CH3:20][Mg]Br.[Cl-].[NH4+]>ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C@H:12]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH3:20])=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 87457533HCID 87457533, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68450007HCID 68450007, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of (R,E)-N-((5-(cyclopropylmethoxy)pyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (6.2 g, 22 mmol) was dissolved into dichloromethane (110 ml). Methyl magnesium bromide (44 ml, 44 mmol, 1.0M in THF) was added to the mixture at −78° C. dropwise. The mixture was stirred for 1 h at −78° C. The mixture was poured into saturated ammonium chloride aqueous solution, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v)) to give 3.2 g (49% yield) of the title compound as a white solid:

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v))

Sources & evidence

ORD record
ord-7a1f22ecae234cd78cde8c82bf8c1b0f
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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