Iodoethane → HCID 21440196, compound

HRID 328967Notes

Reaction equation

HRID 328967 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[SH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:35](I)[CH3:36]>>[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[S:21][CH2:35][CH3:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate2×HCID 21440227HCID 21440227, compound

Product 1

HCID 21440196HCID 21440196, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 4-benzyl-3-mercapto-5-sulfamylbenzoic acid (1.0 g), sodium hydrogen carbonate (0.3 g), sodium dithionite (0.3 g), ethyl iodide (1.0 ml) and saturated sodium hydrogen carbonate solution (8 ml) is stirred at 70° C for 3 hours. After cooling, the precipitated sodium 4-benzyl-3-ethylthio-5-sulfamylbenzoate is collected by filtration and washed with a minor amount of icecold water. After drying, the sodium salt is dissolved in hot water (10 ml), and the solution is clarified by the filtration hot in the presence of decolorizing carbon. The solution is acidified with conc. hydrochloric acid (0.5 ml) to precipitate the 4-benzyl-3-ethylthio-5-sulfamylbenzoic acid. The acid is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, the compound is obtained with a melting point of 234° -235° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated sodium 4-benzyl-3-ethylthio-5-sulfamylbenzoate is collected by filtration
  3. washwashed with a minor amount of icecold water
  4. customAfter drying
  5. dissolutionthe sodium salt is dissolved in hot water (10 ml)
  6. filtrationthe solution is clarified by the filtration hot in the presence of decolorizing carbon
  7. customto precipitate the 4-benzyl-3-ethylthio-5-sulfamylbenzoic acid
  8. filtrationThe acid is collected by filtration
  9. washwashed with water
  10. customdried
  11. customAfter recrystallization from aqueous ethanol
  12. customthe compound is obtained with a melting point of 234° -235° C.

Sources & evidence

ORD record
ord-3799cee7485445beb7332343b2fe86e6
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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