Hydrochloric Acid → HCID 9814932, compound

HRID 347916Notes

Reaction equation

HRID 347916 reaction equation
Cl.[O:2]=[C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]2[S:15][C:16](C(O)=O)=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=[CH:4]1.[OH-].[Na+]>O1CCOCC1>[C:18]1([C:17]2[C:6]3[CH:5]=[CH:4][C:3](=[O:2])[N:8]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:7]=3[S:15][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21083991HCID 21083991, compound

Product 1

HCID 9814932HCID 9814932, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2M HCl(aq) (10 mL) was added to a solution of the compound of Example 59 (300 mg, 0.864 mmol) in dioxane (30 mL) and the mixture heated at reflux for 16 h. The cooled reaction mixture was poured into 10% NaOH(aq) (50 mL) and extracted with DCM (2×50 mL) The combined organic fractions were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid in quantitative yield. δH (CDCl3) 7.83 (1H, d, J 9 Hz), 7.7–7.35 (10 H, m), 6.80 (1H, s), 6.67 (1H, d, J 9 Hz). m/z (ES+) 304 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  3. customThe cooled reaction mixture
  4. extractionextracted with DCM (2×50 mL) The combined organic fractions
  5. dry with materialwere dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdc0f13c3b0c49d8969aeab8244fdac5
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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