Acetone → Methyl 2-chloro-6-fluorobenzthioimidate hydroiodide

HRID 2269659

Reaction equation

HRID 2269659 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[S:6])[NH2:5].[CH3:12]C(C)=O.[I:16]C>C(#N)C.O>[IH:16].[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([S:6][CH3:12])=[NH:5]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6328Methyl iodideHCID 77452422-Chloro-6-fluorobenzene-1-carbothioamide

Product 1

HCID 18347932Methyl 2-chloro-6-fluorobenzthioimidate hydroiodideYield 46.9%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Into a 50 mL three necked round bottom flask equipped with a magnetic stirrer was added 2-chloro-6-fluorobenzthioamide (3.78 g, 20 mmol) and acetone (20 mL). Dropwise was added iodomethane (2.84 g, 1.24 mL, 20 mmol) and the mixture was allowed to stir at room temperature overnight with monitoring via HPCL (60/40 acetonitrile/water). The solids were removed via filtration and washed with small portions of acetone to give methyl 2-chloro-6-fluorobenzthioimidate hydroiodide as a light yellow solid: 3.1 g (46.9% yield): 1H NMR (DMSO-d6) δ7.7 (m, 1H), 7.5 (m, 2H), 2.7 (s, 3H).

Workup

  1. customThe solids were removed via filtration
  2. washwashed with small portions of acetone

Sources & evidence

ORD record
ord-67d5220cc59c4cfab38fbd25bef74308
Source dataset
uspto-grants-2001_12
Patent number
US06329528B1

Linked notes

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