Pyridine → HCID 86651700, compound

HRID 341361Notes

Reaction equation

HRID 341361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CC=CC=1.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:23]([Cl:22])=[O:25])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7544N-Phenyl-m-anisidineHCID 94429Triphosgene

Product 1

HCID 86651700HCID 86651700, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 3-methoxy-N-phenylaniline (100.0 mg, 0.502 mmol) and pyridine (0.102 mL, 1.267 mmol) in DCM (500 mL) was added triphosgene (120.0 mg, 0.406 mmol). The solution was allowed to warm up to room temperature and stirred overnight. The organic solvent was evaporated. The residue was dissolved in ethyl acetate, washed with water, brine, dried over MgSO4 and concentrated to provide the title compound (105.0 mg). LCMS m/z=261.9 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.79 (s, 3H), 6.90-7.31 (m, 3H), 7.32-7.52 (m, 4H), 7.52-7.70 (m, 2H).

Workup

  1. customThe organic solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c1433ee1a4dc4d6cb5540710689085e1
Source dataset
uspto-grants-2014_11
Patent number
US08895776B2

Reaction notes

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