Trichloromethanethiol → 1,1-Dimethylethyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)-1-piperazinecarboxylate

HRID 2263353Notes

Reaction equation

HRID 2263353 reaction equation
[NH2:1][C:2](=[NH:16])[N:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:17][C:18]([SH:21])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:17][C:18]1[S:21][N:1]=[C:2]([N:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]2)[N:16]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 15197650Tert-butyl 4-carbamimidoylpiperazine-1-carboxylate

Product 1

HCID 665236951,1-Dimethylethyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)-1-piperazinecarboxylateYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[amino(imino)methyl]piperazine-1-carboxylate (1.50 g, 5.67 mmol) and perchloromethyl mercaptan (0.609 ml, 5.67 mmol) in dichloromethane (20 ml) was added dropwise a solution of sodium hydroxide (0.907 g, 22.7 mmol) in water (2.5 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then 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 1.03 g (59.5%) of the desired product as a solid.

Workup

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

Sources & evidence

ORD record
ord-457bab2709b24d4496d234e6ab42e904
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…