Pyridine → HCID 68569577, compound

HRID 747615Notes

Reaction equation

HRID 747615 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17].N1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([S:34](Cl)(=[O:36])=[O:35])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>C1COCC1.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:34]([C:28]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=2)(=[O:36])=[O:35])=[C:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH:4]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 68567469HCID 68567469, compound

Product 1

HCID 68569577HCID 68569577, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 0.57 g of (2-amino-5-chlorophenyl)(2-methoxyphenyl)methane dissolved in 5 ml of THF are successively added 0.2 ml of pyridine and 0.547 g of 3,4-dimethoxybenzenesulfonyl chloride, and the mixture is left for 18 hours at room temperature. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with dichloromethane, to give 0.832 g of the expected product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on a column of silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4cc1a6e908474f43b4ac22fbde4b5292
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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