Triethylamine → 3-(4-Chloro-2-methylphenyl)-2-ethylsulfanyl-3,5-dihydroimidazol-4-one

HRID 1449616Notes

Reaction equation

HRID 1449616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[C:4]([CH3:11])[CH:3]=1.Cl.[NH2:13][CH2:14][C:15]([NH2:17])=[O:16].[CH2:18](N(CC)CC)[CH3:19]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:10])[NH:13][CH2:14][C:15]([NH2:17])=[O:16])=[C:4]([CH3:11])[CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:15](=[O:16])[CH2:14][N:13]=[C:9]2[S:10][CH2:18][CH3:19])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 900213-Chloro-6-isothiocyanatotolueneHCID 2723639Glycinamide hydrochloride

Product 2

HCID 442957763-(4-Chloro-2-methylphenyl)-2-ethylsulfanyl-3,5-dihydroimidazol-4-oneHCID 536560542-[3-(4-Chloro-2-methylphenyl)-thioureido]-acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-[3-(4-Chloro-2-methylphenyl)-thioureido]-acetamide was prepared by the procedure described in Example 11 using 18.36 g of 4-chloro-2-methylphenylisothiocyanate, 11.05 g of glycinamide hydrochloride, 10.1 g of triethyl amine, and 300 mL of chloroform. 21.4 Grams of the desired compound was obtained, m.p. 170°-172° C. (dec.). Mass spectrum (El, M.+) m/z 257/259. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.38 (s, 1H), 7.62 (broad s, 1H), 7.45 (s, 1H), 7.35 (d, 1H), 7.32 (d, 1H), 7.21 (m, 1H), 7.12 (s, 1H), 4.06 (d, 2H), and 2.17 ppm (s, 3H).

Sources & evidence

ORD record
ord-e9b1c0110f6445ac9f3795b1a26ef577
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

Loading…