5-Chloro-2-methylphenyl isothiocyanate → HCID 53995114, compound

HRID 1449597Notes

Reaction equation

HRID 1449597 reaction equation
[NH2:1][CH2:2][C:3]([NH2:5])=[O:4].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([N:13]=[C:14]=[S:15])[CH:12]=1>C(Cl)(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([NH:13][C:14](=[S:15])[NH:1][CH2:2][C:3]([NH2:5])=[O:4])[CH:12]=1

Participants

4

Reactant 2

HCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 69020Glycinamide

Product 1

HCID 53995114HCID 53995114, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Glycinamide (10.08 g) and 5-chloro-2-methylphenyl-isothiocyanate (23 g) were heated at reflux in chloroform (300 mL) for 30 minutes. The mixture was then stirred at ambient temperature for 3 hours. The precipitated solid was collected by filtration, washed with chloroform and air dried to give 2-[3-(5-chloro-2-methylphenyl)thioureido]-acetamide (28.5 g), m.p. 162°-164° C. Mass spectrum (El, M.+) m/z 257/259. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.46 (s, 1H), 7.83 (s, 1H), 7.51 (d, 2H), 7.24 (d, 1H), 7.24 (d, 1H), 7.18 (d, 1H), 7.15 (m, 2H), 4.06 (d, 2H), and 2.16 ppm (s, 3H).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with chloroform and air
  3. customdried

Sources & evidence

ORD record
ord-1a6af56e0a3d4da3943e9038d8a0df61
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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