Hydrochloric Acid → HCID 67499337, compound

HRID 661365Notes

Reaction equation

HRID 661365 reaction equation
[F:1][C:2]1([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.Cl>O1CCOCC1>[F:1][C:2]1([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[CH2:3][CH2:4][C:5](=[O:6])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67499044HCID 67499044, compound

Product 1

HCID 67499337HCID 67499337, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 27B (3.55 g, 14.59 mmol) in dioxane (40 mL) was added 1M HCl (100 mL). The reaction mixture was stirred overnight at ambient temperature, quenched with 10M NaOH (10 mL) and extracted with three portions of 1:1 ethyl acetate-hexanes. The combined organic layers were concentrated. The resulting residue was chromatographed on silica gel eluting with 0%-20% ethyl acetate-hexane to obtain the title compound (2.15 g, 74%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.82-7.95 (m, 2H), 2.61-2.72 (m, 6H), 2.24-2.42 (m, 2H).

Workup

  1. customquenched with 10M NaOH (10 mL)
  2. extractionextracted with three portions of 1:1 ethyl acetate-hexanes
  3. concentrationThe combined organic layers were concentrated
  4. customThe resulting residue was chromatographed on silica gel eluting with 0%-20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-eebd7b007d61439aa51c3bb970f285d8
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

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