Triethylamine → 3-(Indan-5-yl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742231Notes

Reaction equation

HRID 742231 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]=[C:11]=[S:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.C([O:16][C:17](=O)[CH2:18][NH:19][CH3:20])C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:17](=[O:16])[CH2:18][N:19]([CH3:20])[C:11]3=[S:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 27593575-isothiocyanato-2,3-dihydro-1H-indene

Product 1

HCID 111959623-(Indan-5-yl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 1 using 7.7 g of indan-5-yl-isothiocyanate, 6.7 g of sarcosine ethyl ester hydrochloride, 12 g of triethyl amine, and 300 mL of chloroform. Crystallization from ethyl acetate afforded the title compound (7.9 g) as a tan solid, m.p. 158-160° C. Anal. Calcd. for C13H14N2O S: C, 63.39; H, 5.73; N,11.37. Found: C, 63.30; H, 5.81; N, 11.31. Mass spectrum (EI, M.+) m/z 246.

Workup

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

Sources & evidence

ORD record
ord-e1706389bbe84f19a79645e0c53da8c0
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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