Methyl iodide → HCID 178504008, compound

HRID 1803169Notes

Reaction equation

HRID 1803169 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[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:16][C:17]([S:18][CH3:2])=[NH:19])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 866499181-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 178504008HCID 178504008, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step Q (3): Iodomethane (1.43 mL, 22.9 mmol) was added to a solution of 1-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (5.48 g, 21.8 mmol) in absolute ethanol (200 mL). The resulting mixture was heated at 70° C. for 3 h. After cooling to rt, the reaction was chilled at −20° C. for 2 h. The precipitate was collected by vacuum filtration. The solid was dried under high vacuum to afford methyl 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (8.40 g, 21.4 mmol, 98% yield) as an off-white solid. LC-MS (M+H)+ 266.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.91 (d, J=2.4 Hz, 1 H), 7.91 (t, J=8.5 Hz, 1 H), 7.64 (dd, J=11.7, 2.0 Hz, 1 H), 7.35 (d, J=7.3 Hz, 1 H), 2.70 (s, 3 H), 2.38 (s, 3 H).

Workup

  1. temperatureAfter cooling to rt
  2. temperaturethe reaction was chilled at −20° C. for 2 h
  3. filtrationThe precipitate was collected by vacuum filtration
  4. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-b71ccf3c8c524d5d9e36b983693e5490
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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