Hydrochloric Acid → 3-{[(p-Chlorobenzyl)thiocarbamoyl]thio}-propionic acid

HRID 1395132Notes

Reaction equation

HRID 1395132 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C1(C)C=CC=CC=1.[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([CH2:19][N:20]=[C:21]=[S:22])=[CH:17][CH:16]=1.Cl>C(N(CC)CC)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:20][C:21]([S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[S:22])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 65143-Mercaptopropionic AcidHCID 194084-chlorobenzyl Isothiocyanate

Product 1

HCID 203402593-{[(p-Chlorobenzyl)thiocarbamoyl]thio}-propionic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.06 g. of 3-mercaptopropionic acid in 5 ml. of toluene and 2.0 g. of triethylamine, there was added with cooling 1.83 g. of p-chlorobenzylisothiocyanate. Two phases formed. The mixture was acidified with 1-N hydrochloric acid and extracted with chloroform. The chloroform phases were washed with water, dried over magnesium sulfate and concentrated. The residue was recrystallized from acetonitrile, and 2.1 g. of 3-{[(p-chlorobenzyl)thiocarbamoyl]thio}-propionic acid having a melting point of 126°-127° C. were obtained.

Workup

  1. temperaturewith cooling 1.83 g
  2. customTwo phases formed
  3. extractionextracted with chloroform
  4. washThe chloroform phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from acetonitrile, and 2.1 g

Sources & evidence

ORD record
ord-1b980c3f17f94dbfabf8ffae9227cce3
Source dataset
uspto-grants-1980_05
Patent number
US04202832

Reaction notes

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