p-Chlorothiophenol → HCID 43135474, compound

HRID 1109744Notes

Reaction equation

HRID 1109744 reaction equation
Cl.ClC1C=C(Cl)C(Cl)=CC=1OCCCONC(N(C(C)C)C(=N)N)=N.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1.[Br:34][CH2:35][CH2:36][CH2:37]Br>[OH-].[Na+]>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33][CH2:37][CH2:36][CH2:35][Br:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 80011,3-DibromopropaneHCID 178457600HCID 178457600, compound

Product 1

HCID 43135474HCID 43135474, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In similar fashion to the synthesis of (XV), 4-chlorothiophenol (28.9 grams, 0.2 mol) was treated with sodium hydroxide (40 mL of 20% aqueous solution) and then combined with 1,3-dibromopropane (160 grams, 0.8 mol) and refluxed for 4 hours. The mixture was cooled, the aqueous layer separated and neutralized with 20% sodium hydroxide solution, and the lower layer washed five times with water and distilled at 1 mm Hg. The main fraction was collected between 120°-130° C. as a colorless oil (47.5 grams, 90%) which crystallized on standing to give 4-chlorothiophenoxy propyl bromide (XIX) is then further reacted with acetohydroxamic acid as described previously in Example 1 and hydrolyzed to give the 3-(4-chlorothiophenoxy)propyloxamine hydrochloride (XX). This in turn is reacted with isopropyl dicyanodiamide as described previously in Example 1 to give the title compound (XXI).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. customthe aqueous layer separated
  4. washthe lower layer washed five times with water
  5. distillationdistilled at 1 mm Hg
  6. customThe main fraction was collected between 120°-130° C. as a colorless oil (47.5 grams, 90%) which
  7. customcrystallized

Sources & evidence

ORD record
ord-3e4bb3c1099f47c1a85ea8a26df5c9c6
Source dataset
uspto-grants-1994_06
Patent number
US05322858

Reaction notes

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