Methyl iodide → HCID 178493242, compound

HRID 1803108Notes

Reaction equation

HRID 1803108 reaction equation
[I:1][CH3:2].[F:3][C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][C:12]([CH3:15])=[N:11]2)[C:7]([O:16][CH3:17])=[CH:6][C:5]=1[NH:18][C:19]([NH2:21])=[S:20]>C(O)C>[IH:1].[F:3][C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][C:12]([CH3:15])=[N:11]2)[C:7]([O:16][CH3:17])=[CH:6][C:5]=1[NH:18][C:19]([S:20][CH3:2])=[NH:21]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866498901-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 178493242HCID 178493242, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step B (5): Iodomethane (0.184 mL, 2.95 mmol) was added to a solution of 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (664 mg, 2.36 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 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (1.05 g, 105% yield) as a white solid. LC-MS (M+H)+ 296.2. 1H NMR (500 MHz, methanol-d4) δ ppm 7.70 (s, 1 H) 6.57 (d, J=10.68 Hz, 1 H) 6.12 (d, J=6.41 Hz, 1 H) 2.74 (s, 3 H) 1.50 (s, 3 H) 1.17 (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-c2967ad637e64f9b8a23312b740348d2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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