p-Toluenesulfonic acid → HCID 10016816, compound

HRID 1722828Notes

Reaction equation

HRID 1722828 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18]C(=O)CCl)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])=[O:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13603691HCID 13603691, compound

Product 1

HCID 10016816HCID 10016816, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloroacetyl-2-[2'-(o-chloroacetoxyphenyl)ethyl]thiazolidine (5.5 g) in dry methanol is treated with p-toluenesulphonic acid (0.5 g) at room temperature for 2 days. The excess of solvent is evaporated in vacuum and then the mixture is diluted with water (80 ml). The crystalline precipitate is collected by filtration, dried in vacuum and recrystallized from Et2O to give 3.9 g of 3-chloroacetyl-2-[2'-(o-hydroxyphenyl)ethyl]thiazolidine m.p. 98° C.

Workup

  1. customThe excess of solvent is evaporated in vacuum
  2. additionthe mixture is diluted with water (80 ml)
  3. filtrationThe crystalline precipitate is collected by filtration
  4. customdried in vacuum
  5. customrecrystallized from Et2O

Sources & evidence

ORD record
ord-0306a39401034b54ac335c09aee24c05
Source dataset
uspto-grants-1989_08
Patent number
US04857643

Reaction notes

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