Methyl iodide → HCID 178504012, compound

HRID 1803113Notes

Reaction equation

HRID 1803113 reaction equation
[I:1][CH3:2].[F:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]([NH2:19])=[S:18])[CH:7]=[CH:8][C:9]=1[N:10]1[C:14]([CH3:15])=[N:13][CH:12]=[N:11]1>C(O)C>[IH:1].[F:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]([S:18][CH3:2])=[NH:19])[CH:7]=[CH:8][C:9]=1[N:10]1[C:14]([CH3:15])=[N:13][CH:12]=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866498921-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 178504012HCID 178504012, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step C (5) [79643-051]: Iodomethane (0.835 mL, 13.4 mmol) was added to a solution of 1-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (3.21 g, 12.8 mmol) in absolute ethanol (100 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-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (4.82 g, 96% yield) as a white solid. LC-MS (M+H)+ 266.0. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.12 (s, 1 H), 7.77 (t, J=8.5 Hz, 1 H), 7.64 (dd, J=11.0, 2.1 Hz, 1 H), 7.37 (dd, J=8.4, 1.4 Hz, 1 H), 2.72 (s, 3 H), 2.36 (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-736a34fac22a4e10b3ba5162e1847ee9
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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