Triethylamine → 1-Butyl-3-(2-chloro-6-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 399606Notes

Reaction equation

HRID 399606 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]=[C:10]=[S:11].[CH2:12]([NH:16][CH2:17][C:18](O)=[O:19])[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>C(Cl)Cl>[CH2:12]([N:16]1[CH2:17][C:18](=[O:19])[N:9]([C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]1=[S:11])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 413376NoName_600HCID 37317252-Chloro-6-Methylphenyl Isothiocyanate

Product 1

HCID 111739861-Butyl-3-(2-chloro-6-methylphenyl)-2-thioxo-imidazolidin-4-oneYield 36.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the procedure described in Example 11 using 6.5 g of 2-chloro-6-methylphenyl-isothiocyanate, 8.5 g of N-butyl glycine, 10.0 g of triethyl amine, and 150 mL of methylene chloride. Purification was achieved by flash chromatography on silica gel (methylene chloride). Crystallization from ethanol afforded the title compound (3.85 g) as a light pink solid, m.p. 97°-100° C. Anal. Calcd. for. C14H17Cl N2O S : C, 56.65; H, 5.77; N, 9.44. Found: C, 56.45; H, 5.67; N, 9.33. Mass spectrum (+FAB, [M+H]+) m/z 297.

Workup

  1. customThe title compound was prepared by the procedure
  2. customPurification
  3. customCrystallization from ethanol

Sources & evidence

ORD record
ord-496d53ad442f47f3b6db05ec5009ec46
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Reaction notes

Loading…