Methyl iodide → HCID 178504022, compound

HRID 1803173Notes

Reaction equation

HRID 1803173 reaction equation
[I:1][CH3:2].[F:3][C:4]1[CH:5]=[C:6]([NH:17][C:18]([NH2:20])=[S:19])[CH:7]=[C:8]([F:16])[C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1>C(O)C>[IH:1].[F:3][C:4]1[CH:5]=[C:6]([NH:17][C:18]([S:19][CH3:2])=[NH:20])[CH:7]=[C:8]([F:16])[C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866499191-(3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 178504022HCID 178504022, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step R (4): Iodomethane (0.413 mL, 6.63 mmol) was added to a solution of 1-(3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (1.7 g, 6.31 mmol) in absolute ethanol (50 mL). The resulting mixture was heated at 70° C. for 3 h. After cooling to rt, the reaction was concentrated in vacuo. The residual volatiles were removed under high vacuum to afford methyl 3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (2.4 g, 5.84 mmol, 92% yield) as a grey solid. LC-MS (M+H)+ 284.0. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.86 (s, 1 H), 7.50 (d, J=8.9 Hz, 2 H), 2.71 (s, 3 H), 2.38 (s, 3 H).

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residual volatiles were removed under high vacuum

Sources & evidence

ORD record
ord-ba44be2d91164b3795d0e1bd45df06d0
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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