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

HRID 377024

반응식

HRID 377024 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85d5aa90d7c74d0da7791aad0ed02f39
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022975

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