1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178457568, 화합물

HRID 2212113노트

반응식

HRID 2212113 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[N:11]=[C:10]2SC)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:18]([O:25][C:26]([NH:28][C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[NH:30])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[NH:11][C:10]2=[N:30][C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[N:28][C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 115873491-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dioneHCID 178457608N-(benzyloxycarbonyl)-N'-isopropylguanidine

생성물 1

HCID 178457568HCID 178457568, 화합물수율 31.8%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
50 °C

실험 절차

To the solution of the crude dione 15 (0.10 g, 0.346 mmol) in 25 ml of dry CHCl3 was added N-(benzyloxycarbonyl)-N′-isopropylguanidine (16) (0.122 g, 0.519 mmol) at room temperature. The reaction mixture was heated at 50° C. for 18 hours and then quenched with water. The mixture was extracted with chloroform and dried over Na2SO4. The CHCl3 was removed in vacuo and the crude product was recrystallized from hexanes/CHCl3 to yield compound 4d as light yellow crystals (51 mg, 0.11 mmol, 31%), mp 211° C. 1H NMR (300 MHz, CDCl3): δ 7.54–7.51(m, 2H), 7.41 (s, 5H), 7.25 (dd, J=8.6 and 2.4 Hz, 1H), 5.25 (s, 2H), 4.12 (m, 1H), 2.46 (d, J=6.6 Hz, 6H). 13C NMR: δ 170.83, 155.86, 153.87, 133.89, 132.56, 132.19, 131.22, 130.42, 129.21, 128.93, 128.65, 128.61, 125.60, 69.24, 45.25, 22.28. MS (m/z): 476 (M+), 370, 316, 314, 236. Anal. (C21H19Cl2N5O4) C, H, Cl, N.

후처리

  1. customquenched with water
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialdried over Na2SO4
  4. customThe CHCl3 was removed in vacuo
  5. customthe crude product was recrystallized from hexanes/CHCl3

출처 및 근거

ORD 기록
ord-56c7c5c73edb422ba351c0bdea064b98
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101902B2

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