Trichloromethanethiol → HCID 18411445, compound

HRID 1107263Notes

Reaction equation

HRID 1107263 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:10]([NH2:12])=[NH:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[Cl:22][C:23]([SH:26])(Cl)Cl>ClCCl>[Cl:22][C:23]1[S:26][N:12]=[C:10]([CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:11]=1

Participants

5

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 18411497HCID 18411497, compound

Product 1

HCID 18411445HCID 18411445, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 2-(3-chlorophenyl)-2-(tetrahydropyran-2-yloxy)acetamidine hydrochloride (12.0 g, 39.51 mmol) in dichloromethane (20 mL) and sodium hydroxide (9.49 g, 0.237 mol, dissolved in 60 mL water) was added a solution of perchloromethyl mercaptan (9.18 g, 49.46 mmol) in dichloromethane (50 mL) over a period of 35 min. The reaction mixture was stirred at ice-cold temperature for a further 1 h and the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6) afforded the title compound as a light yellow oil (8.4 g, 61.5%). 1H-NMR (CDCl3) δ7.56 (d, J=6.9 Hz, 1H, Ar--H), 7.39-7.44 (m, 1H, Ar--H), 7.28-7.32 (m, 2H, Ar--H),6.08 and 6.03 (s, 0.5H each, α-H), 4.84 and 4.72 (t, J=3.1Hz, 0.5H each, OCHO), 3.49-3.92 (m, 2H, OCH2), 1.55-1.94 (m, 6H, 3CH2).

Workup

  1. customthe organic layer was collected
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography on silica gel using
  6. additiona mixture of hexane and ethyl acetate (94/6)

Sources & evidence

ORD record
ord-481b687af6db4224af92faede64a7f01
Source dataset
uspto-grants-2000_05
Patent number
US06060472

Reaction notes

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