Water → HCID 59310059, compound

HRID 1512973Notes

Reaction equation

HRID 1512973 reaction equation
O.S(=O)(=O)(O)O.[Cl:7][C:8]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][C:9]=1[NH2:10].[C:16]1([C:22](O)([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[Cl:7][C:8]1[CH:14]=[CH:13][C:12]([S:15][C:22]([CH3:24])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:23])=[CH:11][C:9]=1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 120532-Phenyl-2-propanolHCID 6406993-amino-4-chlorobenzenethiol

Product 1

HCID 59310059HCID 59310059, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of water (10 mL) and concentrated sulfuric acid (10 mL) was added 2-chloro-5-mercaptoaniline (1.6 g) at room temperature, and the mixture was stirred for 15 minutes. To the mixture was added a solution of 2-phenyl-2-propanol (1.36 g) in tetrahydrofuran (10 mL) in a dropwise manner, and the mixture was stirred at room temperature for 30 minutes. 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 (1.62 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-b8e210f98fd24b6fbd66f5d3e45f1c01
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

Loading…