Chloroform → 2-[N-(benzenesulfonyl)anilino]acetic acid

HRID 1834351Notes

Reaction equation

HRID 1834351 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(Cl)(Cl)Cl.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:18]1([S:24]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]([OH:11])=[O:10])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 66025N-Phenylglycine

Product 1

HCID 8468372-[N-(benzenesulfonyl)anilino]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.7 Parts of N-phenylglycine and 5 parts of sodium hydroxide are dissolved in 30 parts of water. Into the resulting solution, 5 parts of chloroform containing 10 parts of benzenesulfonyl chloride is dropped with stirring. After the dropping, the resulting mixture is stirred at room temperature for 4 hours and then at 50° C for 30 minutes. Subsequently, the aqueous layer is separated from the reaction mixture and then acidified with hydrochloric acid to form an oily substance. By rubbing on the inner wall of a flask with spatula, crystallized products are formed. The crystals are recrystallized from a mixed solvent comprising methanol and water to obtain 4.2 parts of N-benzenesulfonyl-N-phenylglycine, m.p. 166°-167° C.

Workup

  1. stirringAfter the dropping, the resulting mixture is stirred at room temperature for 4 hours
  2. customSubsequently, the aqueous layer is separated from the reaction mixture
  3. customto form an oily substance
  4. customBy rubbing on the inner wall of a flask with spatula
  5. customcrystallized products
  6. customare formed
  7. customThe crystals are recrystallized from a mixed solvent

Sources & evidence

ORD record
ord-d8301f324c3648688deea2176b899628
Source dataset
uspto-grants-1978_01
Patent number
US04070176

Reaction notes

Loading…