Trichloromethanethiol → 1-(5-Chloro-1,2,4-thiadiazol-3-yl)-4-(phenylmethyl)piperazine

HRID 2263352Notes

Reaction equation

HRID 2263352 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:16])[NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]([SH:21])(Cl)Cl.[OH-].[Na+]>C(Cl)Cl.O>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[C:18]([Cl:17])[S:21][N:16]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 1609034-Benzylpiperazine-1-carboximidamide

Product 1

HCID 687769531-(5-Chloro-1,2,4-thiadiazol-3-yl)-4-(phenylmethyl)piperazineYield 29.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzylpiperazine-1-carboximidamide (2.50 g, 11.5 mmol) and perchloromethyl mercaptan (1.24 ml, mmol) in methylene chloride (12 ml) was added dropwise a solution of sodium hydroxide (1.84 g, 46.0 mmol) in water (5 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The reaction mixture was poured to water, and the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 1.00 g (29.6%) of the desired product as an oil.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6f717ce8f07846858e3489bffe868fe4
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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