Trichloromethanethiol → HCID 86625483, compound

HRID 2263002Notes

Reaction equation

HRID 2263002 reaction equation
Cl.[NH2:2][C:3](=[NH:18])[N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.[Cl:19][C:20]([SH:23])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:19][C:20]1[S:23][N:2]=[C:3]([N:4]2[CH2:5][CH2:6][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:8][CH2:9]2)[N:18]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 72206805HCID 72206805, compound

Product 1

HCID 86625483HCID 86625483, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {1-[amino(imino)methyl]piperidin-4-yl}carbamate hydrochloride (1.50 g, 5.38 mmol) and perchloromethyl mercaptan (0.578 ml, 5.38 mmol) in dichloromethane (20 ml) was added dropwise a solution of sodium hydroxide (0.861 g, 21.5 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 590 mg (34.3%) 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-5d83f4a873ac42ffbe4ce170fde98bf8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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