Sodium Hydroxide → [4-(1-Methylpiperidin-4-ylidene)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetic acid

HRID 389033Notes

Reaction equation

HRID 389033 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])[CH2:6][S:7][C:8]1[CH:9]=[CH:10][C:11]2[O:20][CH2:19][C:18]3[CH:17]=[CH:16][S:15][C:14]=3[CH:13]([CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:12]=2[CH:28]=1>C(O)C>[CH3:27][N:24]1[CH2:25][CH2:26][C:21](=[C:13]2[C:12]3[CH:28]=[C:8]([S:7][CH2:6][C:5]([OH:29])=[O:4])[CH:9]=[CH:10][C:11]=3[O:20][CH2:19][C:18]3[CH:17]=[CH:16][S:15][C:14]2=3)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86649444Methyl[4-(1-methylpiperidin-4-yl)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetate

Product 1

HCID 68490446[4-(1-Methylpiperidin-4-ylidene)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetic acidYield 50.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous sodium hydroxide (1.4 g, 680 mmol) solution was added to an ethanol (40 mL) solution of the compound obtained in Example 24 (2.9 g, 6.7 mmol), and the mixture was refluxed while heating for 2 hours. After allowing the mixture to cool in the air, the solvents were distilled off under a reduced pressure, water was added to the residue, and the mixture was neutralized with hydrochloric acid. The precipitated crystals were separated by filtration and dried, to give 1.3 g (50%) of the captioned compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewhile heating for 2 hours
  3. temperatureto cool in the air
  4. distillationthe solvents were distilled off under a reduced pressure, water
  5. additionwas added to the residue
  6. customThe precipitated crystals were separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-db03ff07f27a4a339233a45dfa203a32
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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