Methylamine → 1-(2-Fluoro-4-iodophenyl)-3-methylurea

HRID 882199Notes

Reaction equation

HRID 882199 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[CH3:12][NH2:13]>>[F:11][C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]([NH:13][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 46132772-Fluoro-4-iodophenyl isocyanate

Product 1

HCID 597173511-(2-Fluoro-4-iodophenyl)-3-methylurea

Procedure

A solution of 4-Iodo-2-fluorophenyl isocyanate (6-1, 5.15 g, 19.6 mmol) in Hexanes (80 ml) was treated with a solution of Methylamine (2M in THF, 9.8 mL, 19.6 mmol, 1.0 eq). A white precipitate formed as the mixture stirred at 23 deg C. for 30 min. The precipitate was collected via filtration and air dried, affording the title compound, N-(2-fluoro-4-iodophenyl)-N′-methylurea (6-2), as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.89 (t, 2H, J=8.6 Hz), 7.47-7.38 (m, 2H), 6.31 (bs, 1H), 4.58 (bs, 1H), 2.88 (d, 3H, J-4.9 Hz). LRMS m/z: Calc'd for C8H8FIN2O (M+H) 295.1, found 294.9.

Workup

  1. customA white precipitate formed as the mixture
  2. filtrationThe precipitate was collected via filtration and air
  3. customdried

Sources & evidence

ORD record
ord-4fefea020ae94d7990eb0747db4f05f5
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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