Dimethyl Sulfoxide → HCID 11172703, compound

HRID 541925Notes

Reaction equation

HRID 541925 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C[S:10]([CH3:12])=O.O>[Cl-].[Na+].O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][S:10][C:12]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])[CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 315773-Aminothiophenol

Product 1

HCID 11172703HCID 11172703, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3-aminobenzenethiol (0.85 mL, 8.0 mmol) in dimethyl sulfoxide (0.57 mL, 8.0 mmol) was heated at 85° C. for 4 h. The reaction mixture was poured into a solution of brine (25 mL) and water (25 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude oil. This material was purified by flash column chromatography to give the desired product (0.97 g, 98%) as a yellow oil. LCMS for C12H13N2S2 (M+H)+: m/z=249.0.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a crude oil
  7. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-2b823565aa9548bf8c95b610edb9a97b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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