Water → Benfuresate

HRID 27643Notes

Reaction equation

HRID 27643 reaction equation
S(Cl)(Cl)=O.[CH2:5]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14](O)=[C:13]([C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])[CH:12]=1)(=[O:9])=[O:8])[CH3:6].O>CN(C)C=O>[CH2:5]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]2[O:20][CH2:19][C:18]([CH3:22])([CH3:21])[C:13]=2[CH:12]=1)(=[O:9])=[O:8])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 233412894-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl ethanesulphonate

Product 1

HCID 3034378BenfuresateYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (4.3 g) was added dropwise to dimethylformamide (13 ml) maintained at about 5° C. To this was quickly added 4-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl ethanesulphonate (9.5 g) from Example 2 in dimethylformamide (13 ml). The reaction mixture was then heated to 100° C. and maintained at that temperature for 4-5 hours, after which it was cooled and poured into water (100 ml). The oil was extracted with diethyl ether, washed with water, dried over magnesium sulphate and evaporated down to give 6.2 g of a brownish oil.

Workup

  1. temperatureThe reaction mixture was then heated to 100° C.
  2. temperaturemaintained at that temperature for 4-5 hours
  3. temperatureafter which it was cooled
  4. extractionThe oil was extracted with diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down

Sources & evidence

ORD record
ord-3dae8ba852554d2e957caec290b2e483
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Reaction notes

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