Triethylamine → 2-[3-(2,6-Dimethylphenyl)-thioureido]-acetamide

HRID 1417740Notes

Reaction equation

HRID 1417740 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]=[S:11].Cl.[NH2:13][CH2:14][C:15]([NH2:17])=[O:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[S:11])[NH:13][CH2:14][C:15]([NH2:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 879762,6-Xylyl isothiocyanateHCID 2723639Glycinamide hydrochloride

Product 1

HCID 539479742-[3-(2,6-Dimethylphenyl)-thioureido]-acetamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,6-dimethylphenyl-isothiocyanate (16.3 g), glycinamide hydrochloride (11.05 g), triethyl amine (12.0 g), and chloroform (250 mL) was heated at reflux for 3 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) and washed with 1N HCl (300 mL) then with water (300 mL). The organic phase was evaporated to dryness, then the residue was stirred with diethyl ether. The solid was collected by filtration and dried to afford 2-[3-(2,6-dimethylphenyl)-thioureido]-acetamide as a solid (18.3 g). Mass spectrum (EI, M.+) m/z 237. This compound was used without further purification in the preparation of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. washwashed with 1N HCl (300 mL)
  6. customThe organic phase was evaporated to dryness
  7. filtrationThe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-179e70ed595d42918d81eaf4ac903308
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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