Water → HCID 59309951, compound

HRID 1512992Notes

Reaction equation

HRID 1512992 reaction equation
S(=O)(=O)(O)O.O.[Cl:7][C:8]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([SH:17])=[CH:11][C:9]=1[NH2:10].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](O)([CH3:28])[CH3:27]>O1CCCC1>[Cl:7][C:8]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([S:17][C:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH3:18])([CH3:28])[CH3:27])=[CH:11][C:9]=1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 591999HCID 591999, compoundHCID 59309723HCID 59309723, compound

Product 1

HCID 59309951HCID 59309951, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To concentrated sulfuric acid (6 mL) was added water (6 mL) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added a solution of 2-chloro-5-mercapto-4-methoxyaniline (0.5 g) and 2-(2-methoxyphenyl)-2-propanol (0.88 g) in tetrahydrofuran (6 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1) to give the title compound (0.3 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-2259cfe1943a4ac2aec64aca8e57a24e
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

Loading…