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

HRID 1417720Notes

Reaction equation

HRID 1417720 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°-1640° C. Mass spectrum (EI, M.+) m/z 257/259. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.46 (s, 1 H), 7.83 (s, 1 H), 7.51 (d, 2 H), 7.24 (d, 1 H), 7.24 (d, 1 H), 7.18 (d, 1 H), 7.15 (m, 2 H), 4.06 (d, 2 H), and 2.16 ppm (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-6fae9032c81f41fbbf9dc1c665e0162e
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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