Potassium Carbonate → Phosphoric Acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl Ester Dimethyl Ester

HRID 1383749

反応式

HRID 1383749 の反応式
Cl[CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:21].[P:22]([O-:28])([O:26][CH3:27])([O:24][CH3:25])=[O:23].[K+].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[CH3:25][O:24][P:22](=[O:23])([O:26][CH3:27])[O:28][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:21]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 110986333-(Chloromethyl)-5,5-diphenylimidazolidine-2,4-dioneHCID 23666574Dimethyl phosphate, potassium salt

生成物 1

HCID 15459543Phosphoric Acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl Ester Dimethyl Ester収率 41.1%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

Thirty grams of 3-(chloromethyl)-5,5-diphenyl-2,4-imidazolidinedione from Step (A), 17.1 g of potassium dimethyl phosphate, 0.6 g of potassium carbonate, and 0.15 g of potassium iodide were slurried into 75 mL of acetonitrile. The reaction mixture was heated at reflux for 3 hours. The solution was filtered to remove potassium chloride precipitate and concentrated to thick oil. Isopropyl alcohol was added to the oil and cooled to 0° C. The product was filtered and dried under vacuum. Sixteen grams of the title compound was obtained (40.9% yield); mp 123.1-124.3° C. Proton nuclear magnetic resonance spectroscopy (1H NMR) deuterated dimethyl sulfoxide (DMSO-d6): 3.6 ppm (d, 6H), 5.3 (d, 2H), 7.3-7.5 (m, 10H), 10.0 (s, 1H); doublets from long range phosphorous coupling.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe solution was filtered
  4. customto remove potassium chloride precipitate
  5. concentrationconcentrated to thick oil
  6. additionIsopropyl alcohol was added to the oil
  7. filtrationThe product was filtered
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-39384ed111e54056b81ed90d5be2440e
出典データセット
uspto-grants-2001_07
特許番号
US06255492B1

関連ノート

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