Triethylamine → 1-Butyl-3-(4-fluorophenyl)-2-thioxo-imidazolidin-4-one

HRID 742276Notes

Reaction equation

HRID 742276 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[CH2:11]([NH:15][CH2:16][C:17](O)=[O:18])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:11]([N:15]1[CH2:16][C:17](=[O:18])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]1=[S:10])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152414-Fluorophenyl isothiocyanateHCID 413376NoName_600

Product 1

HCID 194253761-Butyl-3-(4-fluorophenyl)-2-thioxo-imidazolidin-4-oneYield 44.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 54 using 7.7 g of 4-fluorophenyl-isothiocyanate, 12.0 g of N-butyl glycine, 15.0 g of triethyl amine, and 250 mL of chloroform. Crystallization from ethanol afforded the title compound (5.9 g) as an off-white solid, m.p. 92°-93° C. Anal. Calcd. for. C13H15F N2O S: C, 58.62; H, 5.68; N, 10.52. Found: C, 58.23; H, 5.65; N, 10.56. Mass spectrum (EI, M.+) m/z 266.

Workup

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

Sources & evidence

ORD record
ord-17930bd053c64f098d7e58e78f4e46ab
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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