Acetic Acid → HCID 19348000, compound

HRID 1637209Notes

Reaction equation

HRID 1637209 reaction equation
[OH-].[Na+].CC([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:16]1[C:17]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:26][C:18]=2[S:19][C:20]=1[C:21]([O:23]CC)=[O:22])=[O:15])=O.C(O)(=O)C>CO.O>[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([C:16]1[C:17]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:26][C:18]=2[S:19][C:20]=1[C:21]([OH:23])=[O:22])=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 19347983HCID 19347983, compound

Product 1

HCID 19348000HCID 19348000, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (3 ml of 1M in water) was added to a suspension of ethyl 3-(2-[(methylcarbonyloxy)methyl]phenylsulfinyl)-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 35--500 mg, 0.98 mmol) in methanol (15 ml). The mixture was heated to reflux for 30 minutes. The resultant solution was cooled, diluted with water and acidified by dropwise addition of acetic acid. The precipitate was isolated by filtration and washing with water. The solid was recrystallised twice by dissolving in hot methanol, and cooling, to give the title compound as a colourless solid (71 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. customThe precipitate was isolated by filtration
  4. washwashing with water
  5. customThe solid was recrystallised twice
  6. dissolutionby dissolving in hot methanol
  7. temperaturecooling

Sources & evidence

ORD record
ord-30b5c496374e49a79cfad1dda8a24b35
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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