Triethylamine → 1-Ethyl-3-(2-ethyl-6-isopropylphenyl)-2-thioxo-imidazolin-4-one

HRID 742253

Reaction equation

HRID 742253 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:4]=1[N:12]=[C:13]=[S:14])[CH3:2].[CH2:15]([NH:17][CH2:18][C:19](O)=[O:20])[CH3:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:15]([N:17]1[CH2:18][C:19](=[O:20])[N:12]([C:4]2[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][CH3:2])[C:13]1=[S:14])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1442342-Ethyl-6-isopropylphenyl isothiocyanateHCID 316542N-Ethylglycine

Product 1

HCID 111853871-Ethyl-3-(2-ethyl-6-isopropylphenyl)-2-thioxo-imidazolin-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared by the procedure described in Example 28 using 20.5 g of 2-ethyl-6-isopropylphenyl-isothiocyanate, 18.4 g of N-ethyl glycine, 20.2 g of triethyl amine, and 300 mL of chloroform. Purification was achieved by flash chromatography on silica gel (5-10 % ethyl acetate in hexane). Crystallization from diethyl ether/hexane afforded pure title compound (7.5 g) as a white solid, m.p. 77°-79° C. Anal. Calcd. for. C16H22N2O S: C, 66.17; H, 7.64; N, 9.65. Found: C, 66.12; H, 7.77; N, 9.69. Mass spectrum i2EI, M.+) m/z 290.

Workup

  1. customPurification
  2. customCrystallization from diethyl ether/hexane afforded pure title compound (7.5 g) as a white solid, m.p. 77°-79° C

Sources & evidence

ORD record
ord-d72dec8fc6484cf0ada8d10c6f41668f
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Linked notes

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