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

HRID 1417739Notes

Reaction equation

HRID 1417739 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-methylphenyl-isothiocyanate, 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 (EI, M.+) m/z 257/259. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.38 (s, 1 H), 7.62 (broad s, 1 H), 7.45 (s, 1 H), 7.35 (d, 1 H), 7.32 (d, 1 H), 7.21 (m, 1 H), 7.12 (s, 1 H), 4.06 (d, 2 H), and 2.17 ppm (s, 3 H).

Sources & evidence

ORD record
ord-9be35a66348241cea7d132a194e7b8ac
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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