Dimethylformamide → 4-[(2-Methylquinolin-4-yl)methoxy]benzenesulphonyl chloride

HRID 2211814Notes

Reaction equation

HRID 2211814 reaction equation
CN(C=O)C.[Na+].[CH3:7][C:8]1[CH:17]=[C:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([O-:29])(=O)=[O:27])=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)([Cl:32])=O>C(Cl)Cl>[CH3:7][C:8]1[CH:17]=[C:16]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([Cl:32])(=[O:29])=[O:27])=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 87940286HCID 87940286, compound

Product 1

HCID 219630384-[(2-Methylquinolin-4-yl)methoxy]benzenesulphonyl chlorideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A catalytic amount of DMF was added to a solution of the 4-[(2-methyl-4-quinolinyl)methoxy]benzenesulfonic acid sodium salt (1.0 g, 2.8 mmol) from step (2a) in thionyl chloride (3.0 ml, 41.0 mmol). The reaction was heated to 60° C. for 2 h, allowed to cool to room temperature, diluted with methylene chloride, concentrated in vacuo, diluted with THF, concentrated in vacuo to give 4-[(2-methyl-4-quinolinyl)methoxy]benzenesulfonyl chloride (0.95 g, 97%) as a light yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with THF
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d63cacd0ecb14400a807d3d45462e527
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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