Imidazole → 5-(2-Benzyloxy-4-iodomethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 1642612

반응식

HRID 1642612 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:25]I.[CH2:27]([O:34][C:35]1[CH:40]=[C:39]([CH2:41]O)[CH:38]=[CH:37][C:36]=1[N:43]1[S:47](=[O:49])(=[O:48])[N:46]([CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:45](=[O:56])[CH2:44]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35]1[CH:40]=[C:39]([CH2:41][I:25])[CH:38]=[CH:37][C:36]=1[N:43]1[S:47](=[O:49])(=[O:48])[N:46]([CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:45](=[O:56])[CH2:44]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 667566545-(2-Benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

생성물 1

HCID 667568095-(2-Benzyloxy-4-iodomethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To slurry of resin-bound PPh3 (850 mg, 2.5 mmol) in DCM (10 mL) at 0° C., in a pressure vessel, is added imidazole (200 mg, 2.8 mmol) and iodine (650 mg, 2.5 mmol). The mixture is vigorously stirred at 0° C. for 30 min. To the mixture is added a solution of 5-(2-benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (550 mg, 1.2 mmol) in DCM (10 mL) dropwise. The vessel is sealed and heated to 45° C., with stirring, for 2 h. The reaction is allowed to cool to ambient temperature and the mixture is filtered through a plug of cotton to remove the resin. The organic solution is washed with saturated Na2SO3 and saturated NaCl, then dried over MgSO4. The solvent is removed under reduced pressure to afford 5-(2-benzyloxy-4-iodomethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one as a white solid, which is used in the next step without further purification: MS (M+H)+=576.

후처리

  1. customThe vessel is sealed
  2. temperatureheated to 45° C.
  3. stirringwith stirring, for 2 h
  4. temperatureto cool to ambient temperature
  5. filtrationthe mixture is filtered through a plug of cotton
  6. customto remove the resin
  7. washThe organic solution is washed with saturated Na2SO3 and saturated NaCl
  8. dry with materialdried over MgSO4
  9. customThe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-cdf6f1fc0d514c389fc6838126f27737
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119666B2

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