HCID 59864849, compound → HCID 59864908, compound

HRID 2423300Notes

Reaction equation

HRID 2423300 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:12]2[NH:13][C:14]([CH3:16])=[N:15][C:11]=2[C:10]=1[N+:19]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[NH2:19][C:10]1[C:11]2[N:15]=[C:14]([CH3:16])[NH:13][C:12]=2[CH:17]=[CH:18][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 59864849HCID 59864849, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59864908HCID 59864908, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under an N2 atmosphere, methyl 2-(3-chloro-4-(2-methyl-4-nitro-1H-benzo[d]imidazol-5-yloxy)phenyl)acetate (0.226 g, 0.601 mmol) was dissolved in ethyl acetate and tin chloride dihydrate (0.543 g, 2.41 mmol) was added. The reaction was allowed to stir at room temperature for 16 h. The reaction was diluted with ethyl acetate and washed with a 10% NaHCO3 (aq) solution. The aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (Na2SO4), filtered, and concentrated in vacuo, and the title compound isolated. LC-MS ESI (pos.) m/z: 346.0 (M+H).

Workup

  1. washwashed with a 10% NaHCO3 (aq) solution
  2. washThe aqueous layer was washed with additional ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c6eb7d6d51942599316e27da199f32b
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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