Dicyclohexylcarbodiimide → S-(4-Fluorobenzyl) 3-benzylthiopropionothioate

HRID 1164500Notes

Reaction equation

HRID 1164500 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([CH2:23][CH2:24][C:25](O)=[S:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][SH:34])=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:16]([CH2:23][CH2:24][C:25](=[S:26])[S:34][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 85171p-Fluorotoluene-alpha-thiolHCID 178526178HCID 178526178, compound

Product 1

HCID 57185058S-(4-Fluorobenzyl) 3-benzylthiopropionothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.18 g (30 mmoles) of dicyclohexylcarbodiimide in 20 ml of methylene chloride were added to a solution, which had been cooled to 0° C., of 5.9 g (30 mmoles) of 3-benzylthiopropionic acid and 4.26 g (30 mmoles) of 4-fluorobenzylmercaptan in 25 ml of methylene chloride, and the mixture was kept overnight at room temperature. After filtering off the dicyclohexylurea and stripping off the solvent, the crude product was purified, first by chromatography, on silica gel, from 1:2 methylene chloride/petroleum ether and then by distillation in a bulb tube.

Workup

  1. filtrationAfter filtering off the dicyclohexylurea
  2. customthe crude product was purified, first by chromatography, on silica gel, from 1:2 methylene chloride/petroleum ether
  3. distillationby distillation in a bulb tube

Sources & evidence

ORD record
ord-c5955d99f3314cb785f20a81376bf8fe
Source dataset
uspto-grants-1983_01
Patent number
US04370342

Reaction notes

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