Hydrochloric Acid → 4-(2-Hydroxyethylsulfanyl)-3-nitrobenzenesulfonamide

HRID 2118578Notes

Reaction equation

HRID 2118578 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].C([O-])(=O)C.[Na+].Cl[C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].Cl>O>[OH:4][CH2:3][CH2:2][S:1][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15672-MercaptoethanolHCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 517045Sodium Acetate

Product 1

HCID 48426344-(2-Hydroxyethylsulfanyl)-3-nitrobenzenesulfonamideYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-mercaptoethanol (1.66 g, 0.02 mol), anhydrous sodium acetate (2 g) and 4-chloro-3-nitrobenzenesulfonamide (2.37 g, 0.01 mol) was heated on the steam bath for about 5 hours. The reaction mixture was diluted with water, acidified with 6N hydrochloric acid and cooled. Filtration and drying gave 2.11 g of a yellow solid that was recrystallized from ethyl acetate, m.p. 150°-152° C.

Workup

  1. temperaturewas heated on the steam bath for about 5 hours
  2. temperaturecooled
  3. filtrationFiltration
  4. customdrying

Sources & evidence

ORD record
ord-311233ea67fe43d78da927b8e5926097
Source dataset
uspto-grants-1987_07
Patent number
US04678855

Reaction notes

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