Allyl bromide → allyl 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydrobromide

HRID 1803182Notes

Reaction equation

HRID 1803182 reaction equation
[CH2:1]([Br:4])[CH:2]=[CH2:3].[F:5][C:6]1[CH:11]=[C:10]([N:12]2[CH:16]=[N:15][C:14]([CH3:17])=[N:13]2)[C:9]([O:18][CH3:19])=[CH:8][C:7]=1[NH:20][C:21]([NH2:23])=[S:22]>C(O)C>[BrH:4].[F:5][C:6]1[CH:11]=[C:10]([N:12]2[CH:16]=[N:15][C:14]([CH3:17])=[N:13]2)[C:9]([O:18][CH3:19])=[CH:8][C:7]=1[NH:20][C:21]([S:22][CH2:3][CH:2]=[CH2:1])=[NH:23]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 866498901-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

Product 1

HCID 178419557allyl 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydrobromideYield 101.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step U (1): Allyl bromide (0.308 mL, 3.55 mmol) was added to a solution of 1-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (1.0 g, 3.55 mmol, from Preparation B, Step B(4)) in absolute ethanol (25 mL). The resulting mixture was heated at 70° C. for 2 h. After cooling to rt, the reaction was concentrated in vacuo. The residual volatiles were removed under high vacuum to afford allyl 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydrobromide (1.45 g, 3.60 mmol, 101% yield) as an off-white solid. LC-MS (M+H)+ 322.0.

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-6e84a5090af34e3889be05dc6ac69f9c
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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