Lithium hydroxide, monohydrate → HCID 86660134, compound

HRID 1746210Notes

Reaction equation

HRID 1746210 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[S:11][C:12](=[O:16])[N:13]([CH3:15])[CH3:14].O.[OH-].[Li+]>C1COCC1.CO.O>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([S:11][C:12](=[O:16])[N:13]([CH3:14])[CH3:15])=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86660135HCID 86660135, compound

Product 1

HCID 86660134HCID 86660134, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 5-bromo-2-dimethylcarbamoylsulfanyl-benzoic acid methyl ester (10.0 g, 31.42 mmol) and lithium hydroxide hydrate (1.98 g, 47.14 mmol) in (1/1/1) THF/MeOH/H2O (70 mL total volume) was stirred at room temperature for 4 h. The reaction mixture was concentrated to remove most organic solvents. The residue was diluted with water (500 mL) and extracted with EtOAc (100 mL), which is discarded. The aqueous layer was acidified to pH 3-4 using 1 N HCl and extracted with EtOAc (2×400 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to provide crude 5-bromo-2-dimethylcarbamoylsulfanyl-benzoic acid which was used directly and without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most organic solvents
  3. additionThe residue was diluted with water (500 mL)
  4. extractionextracted with EtOAc (100 mL), which
  5. extractionextracted with EtOAc (2×400 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-79920c9aab65474db187a089d2bb94fe
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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