1-Chloro-2,4-Dinitrobenzene → [(2,4-Dinitrophenyl)thio]acetic acid

HRID 74052

Reaction equation

HRID 74052 reaction equation
CCN(CC)CC.[SH:8][CH2:9][C:10]([OH:12])=[O:11].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].O>O1CCOCC1>[N+:20]([C:17]1[CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=[CH:19][C:18]=1[S:8][CH2:9][C:10]([OH:12])=[O:11])([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 1133Thioglycolic AcidHCID 8471Triethylamine

Product 1

HCID 60055[(2,4-Dinitrophenyl)thio]acetic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Et3N (1.5 g, 15 mmol) and mercapto-acetic acid (1 g, 11 mmol) were added to a solution of 1-chloro-2,4-dinitrobenzene (2.26 g, 10 mmol) in 1,4-dioxane (50 mL) at room temperature. After stirring at room temperature for 5 h, H2O (100 mL) was added. The resulting suspension was extracted with ethyl acetate (100 mL×3). The ethyl acetate extract was washed with water and brine, dried over Na2SO4 and concentrated to give 2-(2,4-dinitrophenylthio)-acetic acid (2.3 g, 74%), which was used without further purification.

Workup

  1. extractionThe resulting suspension was extracted with ethyl acetate (100 mL×3)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79bf3a81e50045199d373ac0dc9767cd
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Linked notes

Loading…