Trichloromethanethiol → 5-Chloro-3-(4-fluorophenyl)-1,2,4-thiadiazole

HRID 1982798Notes

Reaction equation

HRID 1982798 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[Cl:12][C:13]([SH:16])(Cl)Cl.[OH-].[Na+]>C(Cl)Cl.O>[Cl:12][C:13]1[S:16][N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([F:2])=[CH:4][CH:5]=2)[N:8]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 124561604-Fluorobenzamidine Hydrochloride

Product 1

HCID 463184735-Chloro-3-(4-fluorophenyl)-1,2,4-thiadiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-fluorobenzamidine hydrochloride (0.385 g) in DCM (5 mL) was added perchloromethyl mercaptan (0.219 mL). The resulting mixture was cooled to 0° C., treated with 6 N NaOH (2 mL) and stirred for 30 min. The resulting mixture was diluted with water (10 mL) and extracted with DCM (20 mL). The organic layer was dried (MgSO4) and concentrated. Chromatography of the residue (0-20% EtOAc-hexanes) gave the title compound as a yellow-orange solid (0.43 g).

Workup

  1. extractionextracted with DCM (20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bf3a0be421c0423789c6b526db293ae2
Source dataset
uspto-grants-2009_06
Patent number
US07541359B2

Reaction notes

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