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

HRID 660543

Reaction equation

HRID 660543 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. slurry of resin-bound PPh3 (850 mg, 2.5 mmol) in CH2Cl2 (10 mL) 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 CH2Cl2 (10 mL) dropwise. The vessel is sealed and heated to 45° C., with stirring, for 2 h. The reaction is allowed to cool to RT and the mixture is filtered through a plug of cotton to remove the resin. The organic solution is washed with sat. Na2SO3 and brine, then dried over MgSO4. The solvent is removed under reduced pressure to afford the title compound as a white solid which is used in the next step without further purification: (M+H)+=576.

Workup

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

Sources & evidence

ORD record
ord-e414390b6c7b4237afa1d6e317f7f2ea
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

Loading…