Triethylamine → 3-(4-t-Butylphenyl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742278Notes

Reaction equation

HRID 742278 reaction equation
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:10]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:21]2=[S:22])=[CH:16][CH:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1405034-tert-Butylphenyl IsothiocyanateHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 194253773-(4-t-Butylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), 4-t-butylphenylisothiocyanate (9.6 g), triethyl amine (10.1 g) and chloroform (250 mL) was heated at reflux for 3 hours. The mixture was cooled to ambient temperature, washed with 2N HCl (2×200 mL), then with water (200 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ethanol to give the title compound (9.9 g), m.p. 156°-158° C. Anal. Calcd. for C14H18N2O S: C, 64.09; H, 6.91; N,10.68. Found: C, 63.83; H, 7.15; N, 10.53. Mass spectrum (EI, M.+) m/z 262.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. washwashed with 2N HCl (2×200 mL)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-b17c712d563f49f0b357d2629d2f0833
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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