Triethylamine → 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one

HRID 742274

Reaction equation

HRID 742274 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[S:25])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:9][C:10](=[O:12])[N:23]([C:20]2[CH:21]=[CH:22][C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=2)[C:24]1=[S:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 869652-(Benzylamino)acetic acidHCID 1410041-Butyl-4-isothiocyanatobenzene

Product 1

HCID 857014301-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-benzyl glycine (8.7 g), 4-n-butylphenyl-isothiocyanate (8.55 g), triethyl amine (5.5 g) and chloroform (150 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (300 mL) and water (2×200 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (11.4 g) as an off-white solid, m.p. 149°-151° C. Anal. Calcd. for. C20H22N2O S: C, 70.97; H, 6.55; N, 8.28. Found: C, 70.81; H, 6.76; N, 8.32. Mass spectrum (EI, M.+) m/z 338.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-977c26f1dbf74b3386fc42f7fa574268
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Linked notes

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