Lithium hydroxide, monohydrate → 4-Bromo-2-dimethylcarbamoylsulfanyl-benzoic acid

HRID 1423910ノート

反応式

HRID 1423910 の反応式
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[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:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([S:11][C:12](=[O:16])[N:13]([CH3:14])[CH3:15])[CH:6]=1

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 59750326Methyl 4-bromo-2-[(dimethylcarbamoyl)sulfanyl]benzoate

生成物 1

HCID 866601314-Bromo-2-dimethylcarbamoylsulfanyl-benzoic acid収率 85.5%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

A mixture of 4-bromo-2-dimethylcarbamoylsulfanyl-benzoic acid methyl ester (2.04 g, 6.42 mmol) and lithium hydroxide hydrate (404 mg, 9.62 mmol) in (1/1/1) THF/MeOH/H2O (21 mL) was stirred at room temperature for 6 h. The reaction mixture was concentrated to remove most organic solvents. The residue was diluted with water (100 mL) and extracted with EtOAc (20 mL), which is discarded. The aqueous layer was acidified to pH 3-4 using 1 N HCl and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to provide 4-bromo-2-dimethylcarbamoylsulfanyl-benzoic acid (1.67 g). 1H NMR (200 MHz, CDCl3): δ ppm)=7.76 (m, 2H), 7.61 (dd, J=8.2, 2.0 Hz, 1H), 3.15 (br s, 3H), 3.06 (br s, 3H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most organic solvents
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with EtOAc (20 mL), which
  5. extractionextracted with EtOAc (2×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-f7691327d2a04df19497c589abde5596
出典データセット
uspto-grants-2015_01
特許番号
US08927591B2

反応ノート

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