Hydrochloric Acid → 2-(4-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33798Notes

Reaction equation

HRID 33798 reaction equation
COC[O:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[S:10][C:9]=2[C:8]([C:19]2[O:20][C:21]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:22][C:23](=[O:25])[CH:24]=2)=[CH:7][CH:6]=1.[I-].[Na+].Cl.[OH-].[Na+]>CC(C)=O>[OH:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[S:10][C:9]=2[C:8]([C:19]2[O:20][C:21]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:22][C:23](=[O:25])[CH:24]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 597974342-(4-Methoxymethoxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

Product 1

HCID 597974352-(4-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(4-Methoxymethoxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one (1.1 g, 2.42 mmol) in acetone (50 ml) was added sodium iodide (0.40 g, 2.66 mmol) and concentrated HCl (3 ml). The dark suspension was stirred at room temperature for 72 hours before the careful addition of 1M sodium hydroxide solution until pH 12 was attained. The mixture was washed with EtOAc (2×50 ml) and then acidified with concentrated HCl until pH 1 whereupon a brown precipitate formed which was filtered off (0.90 g, 90%) and corresponded to the title compound. m/z (LC-MS, ESP): RT=4.39 min, (M++1)=456

Workup

  1. washThe mixture was washed with EtOAc (2×50 ml)
  2. customformed which
  3. filtrationwas filtered off (0.90 g, 90%)

Sources & evidence

ORD record
ord-347c25ab193b4ff6b3553ad8daa00ef9
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

Loading…