p-Toluenesulfonic acid → HCID 10016816, compound

HRID 2291910Notes

Reaction equation

HRID 2291910 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-toluensulphonic 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-600511942b044e99baab1760af373f17
Source dataset
uspto-grants-1989_01
Patent number
US04798898

Reaction notes

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