HCID 59864878, compound → HCID 59864873, compound

HRID 2423304Notes

Reaction equation

HRID 2423304 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:26]([N+:27]([O-])=O)=[CH:25][C:12]2[N:13]=[C:14]([CH3:24])[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=2[CH:10]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[NH2:27][C:26]1[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:3][C:2]=2[Cl:1])=[CH:10][C:11]2[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:14]([CH3:24])=[N:13][C:12]=2[CH:25]=1

Participants

5

Reactant 2

HCID 59864878HCID 59864878, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59864873HCID 59864873, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Under an N2 atmosphere, methyl 2-(3-chloro-4-(2-methyl-6-nitro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-benzo[d]imidazol-5-yloxy)phenyl)acetate (0.220 g, 0.435 mmol) was dissolved in ethyl acetate (10 mL) and tin chloride dihydrate (0.392 g, 0.174 mmol) was added. The reaction was allowed to stir at room temperature for 2.5 h. The reaction was diluted with 10% NaHCO3 (aq) and ethyl acetate. The layers were separated and the organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo, afforded the title compound. LC-MS ESI (pos.) m/z: 476.0 (M+H).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2cfe8a909e24121852fb2e0ead143c6
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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