Hydrochloric Acid → HCID 59596261, compound

HRID 2264775Notes

Reaction equation

HRID 2264775 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:19]2[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=2)([C:11]2[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([Cl:18])[CH:12]=2)[N:3]=1.[CH3:26]OC1C=C([Mg]Br)C=CC=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:17][C:15]1[CH:16]=[C:11]([C:4]2([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([NH2:1])=[N:3]2)[CH:12]=[C:13]([Cl:18])[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59596250HCID 59596250, compoundHCID 178490745HCID 178490745, compound

Product 1

HCID 59596261HCID 59596261, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(E)-N-((2-cyanophenyl)(2,6-dichloropyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide (Scheme #19, B, 0.69 g, 1.81 mmol) was dissolved in dry tetrahydrofuran (20 mL) at 0° C. to which a solution of 3-methoxyphenylmagnesium bromide (1.0 M in tetrahydrofuran, 5.44 mL, 5.44 mmol) in tetrahydrofuran was added. The reaction was stirred for 50 minutes and then quenched by addition of saturated aqueous ammonium chloride (25 mL), then further diluted with saturated aqueous sodiumhydrogen carbonate and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated. The residue was dissolved in methanol (20 mL) and treated with hydrochloride (1.0 M in diethyl ether, 3.63 mL, 3.63 mmol) for 1.5 h and then treated with saturated aqueous sodiumhydrogen carbonate and washed with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated. Purification by flash chromatography using ethyl acetate afforded 0.621 g (89% yield) of the title compound. 1H NMR (CDCl3) δ 7.59-7.43 (m, 4 H), 7.29-7.20 (m, 3 H), 6.89-6.87 (m, 3 H), 3.75 (s, 3 H). MS (AP) m/z 384 [M+1]+.

Workup

  1. additionwas added
  2. customquenched by addition of saturated aqueous ammonium chloride (25 mL)
  3. additionfurther diluted with saturated aqueous sodiumhydrogen carbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in methanol (20 mL)
  8. washwashed with ethyl acetate
  9. washThe organic phase was washed with brine
  10. dry with materialdried over sodium sulfate
  11. customevaporated
  12. customPurification by flash chromatography

Sources & evidence

ORD record
ord-fac93ef709e74fa3984bfbc34e99179c
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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