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

HRID 1746184노트

반응식

HRID 1746184 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 866601314-Bromo-2-dimethylcarbamoylsulfanyl-benzoic acid수율 85.5%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c28cf958f44247daa6933c7f5a7370bf
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09149476B2

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