Methanol → HCID 454853, compound

HRID 260473Notes

Reaction equation

HRID 260473 reaction equation
C(OO)(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)C(O)=O.[Mg].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([NH2:27])=S)=[C:19]2C1C=CC=CC=1.[S:34]([O-])([O-])(=[O:36])=S.[Na+].[Na+].C[OH:42]>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([NH2:27])=[O:42])=[C:19]2[S:34]([C:2]1[CH:3]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:36]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 24477Sodium ThiosulfateHCID 9815656Magnesium monoperoxyphthalic acidHCID 14567454HCID 14567454, compound

Product 1

HCID 454853HCID 454853, compound

Conditions

Temperature
20 °C

Procedure

A solution of magnesium monoperoxyphthalic acid (85% peracid) (11.8 mg, 0.024 mmol) in methanol (2 mL) was added dropwise to a solution of 5-chloro-3-phenylthioindole-2-carboxamide (14.5 mg, 0.048 mmol) in methanol (2 mL) at 0° C. The reaction was stirred at 20° C. for 4 hours. A solution of 10% aqueous sodium thiosulfate was added and the reaction stirred vigorously for 10 minutes. Methanol was removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate extract was washed with brine and dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel with 30-40% ethyl acetate in hexane. The title compound was obtained as a white solid. NMR, (DMSO-d6, 300 MHz) δ12.53(1H, s), 8.35(1H,br s), 8.08(1H,br s), 7.83(1H,d,J=2 Hz), 7.71(2H,d,J=8 Hz), 7.52(4H,m), 7.30(1H,dd,J=9,2 Hz).

Workup

  1. stirringthe reaction stirred vigorously for 10 minutes
  2. customMethanol was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product was purified by column chromatography on silica gel with 30-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5f46afc60e124bf2bc6f378f252768ad
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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