N-Acetylimidazolidinone → HCID 10308497, compound

HRID 2187661Notes

Reaction equation

HRID 2187661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:5]2.C([N:21]1[CH2:25][CH2:24][NH:23][C:22]1=O)(=O)C>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[C:5]2[C:22]1[NH:23][CH2:24][CH2:25][N:21]=1

Participants

4

Reactant 2

HCID 79350N-AcetylimidazolidinoneHCID 27629635-CHLORO-2-(PHENYLMETHYL)-INDOLE

Product 1

HCID 10308497HCID 10308497, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.42 g (10 mmol) 5-chloro-2-benzylindole and 1.28 g (10 mmol) 1-acetyl-imidazolidine-2-one (0.1 mol) is added to phosphorus oxychloride (10 ml) and heated to 60° C. for 5 hours. After evaporation of phosphorus oxychloride the residue is treated with ethanol (14 ml) and heated to reflux for 3.5 hours. Ethanol is evaporated. The residue is purified by chromatography to obtain the hydrochloride. The base is obtainable by treatment with 2N sodium hydroxide to pH 11. The solid is filtered off and dried in vacuo. Hydrochloride, m.p. 299-300° C., M.S. (Ei 70 ev) m/Z M=309.

Workup

  1. customAfter evaporation of phosphorus oxychloride the residue
  2. additionis treated with ethanol (14 ml)
  3. temperatureheated
  4. temperatureto reflux for 3.5 hours
  5. customEthanol is evaporated
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-7be9f9623b3349648c940d2d687f8f64
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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