Ethylamine → N-(5-fluoro-2-methylphenyl)-N'-ethylthiourea

HRID 720480Notes

Reaction equation

HRID 720480 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=[S:10])[CH:7]=1.[CH2:12]([NH2:14])[CH3:13]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]([NH:14][CH2:12][CH3:13])=[S:10])[CH:7]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 5194435-Fluoro-o-tolyl Isothiocyanate

Product 1

HCID 21893719N-(5-fluoro-2-methylphenyl)-N'-ethylthiourea

Procedure

5-Fluoro-2-methylphenyl isothiocyanate (16.7 g; 0.1 mol) was added dropwise to aqueous ethylamine (120 mL of 70% solution). The mixture was stirred for 2 hour at ambient temperature. Excess ethylamine was removed under a stream of nitrogen. The residue was diluted with water. The solids were collected by filtration, washed with water and dried. The solid was dissolved in ether and washed with water. The organic phase was dried over anhydrous magnesium sulfate then evaporated to dryness to give N-(5-fluoro-2-methylphenyl)-N′-ethylthiourea (18.5 g), m.p. 93–95° C. Mass spectrum; (El, M.+) m/z 212. 1H-NMR (DMSO-d6; 300 MHz): δ 9.01 (br s, 1H), 7.66 (br s, 1H), 7.25–7.18 (m, 2H), 6.96 (m, 1H), 3.45 (m, 2H), 2.13 (s, 3H), and 1.09 ppm (t, 3H).

Workup

  1. customExcess ethylamine was removed under a stream of nitrogen
  2. additionThe residue was diluted with water
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. customdried
  6. dissolutionThe solid was dissolved in ether
  7. washwashed with water
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. customthen evaporated to dryness

Sources & evidence

ORD record
ord-9621857a55384e0cb3e223e4f1320a44
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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