Triethylamine → 4-Imidazolidinone, 3-(diphenylmethyl)-1-methyl-2-thioxo-

HRID 1957312Notes

Reaction equation

HRID 1957312 reaction equation
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[CH:10]([N:23]=[C:24]=[S:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:10]([N:23]1[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:24]1=[S:25])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 520742Benzhydryl isothiocyanate

Product 1

HCID 111506254-Imidazolidinone, 3-(diphenylmethyl)-1-methyl-2-thioxo-Yield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), benzhydryl-isothiocyanate (11.25 g), triethyl amine (12 g) and chloroform (200 mL) was heated at reflux for 5 hours. The mixture was cooled to ambient temperature, washed with 1N HCl (2×200 mL), then with water (200 mL) The organic phase was evaporated to dryness. The residue was crystallized from ethanol to give the title compound (7.40 g) as an off-white solid, m.p. 139°-141° C. Anal. Calcd. for C17H16N2O S: C, 68.89; H, 5.44; N, 9.45. Found: C, 68.92; H, 5.43; N, 9.58. Mass spectrum (EI, M.+) m/z 296.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. washwashed with 1N HCl (2×200 mL)
  4. customwith water (200 mL) The organic phase was evaporated to dryness
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-a0cec222b0794bc1a1dab894d14b4bf6
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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