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

HRID 720478Notes

Reaction equation

HRID 720478 reaction equation
[Cl: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]>>[Cl: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 295195-Chloro-2-methylphenyl isothiocyanate

Product 1

HCID 4937761N-(5-chloro-2-methylphenyl)-N'-ethylthiourea

Procedure

5-Chloro-2-methylphenyl isothiocyanate (18.3 g; 0.1 mol) was added dropwise to aqueous ethylamine (200 mL of 70% solution). The mixture was stirred for 18 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 to give N-(5-chloro-2-methylphenyl)-N ′-ethylthiourea (18.9 g). A sample crystallized from ethyl acetate afforded a solid, m.p. 120–122° C. Mass spectrum;; FAB (M+H)+ m/z 228. 1H-NMR (DMSO-d6; 300 MHz): δ 9.01 (br s, 1H), 7.67 (br s, 1H), 7.35 (br s, 1H), 7.25–7.16 (m, 2H), 3.44 (m, 2H), 2.13 (s, 3H), and 1.08 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

Sources & evidence

ORD record
ord-0164d2d797474b9ba7bcb8496c95908b
Source dataset
uspto-grants-2006_11
Patent number
US07135492B2

Reaction notes

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