Methanesulfonyl chloride → HCID 14800671, compound

HRID 729023Notes

Reaction equation

HRID 729023 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([NH2:23])=O)=[CH:15][CH:14]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]#[N:23])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14800670HCID 14800670, compound

Product 1

HCID 14800671HCID 14800671, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(4-(2-Quinolinylmethyloxy)benzyl)benzamide (0.03 mol) in pyridine (150 ml) with methane sulfonyl chloride (0.06 mol) is heated at 70° C. for several hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The ethyl acetate extract is dried (magnesium sulfate) then applied to a silica gel column. The product is isolated by elution with the appropriate mixture of ethyl acetate and petroleum ether to obtain 3-(4-(2-quinolinylmethyloxy)benzyl)benzonitrile.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialis dried (magnesium sulfate)
  4. customThe product is isolated by elution with the appropriate mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-c3151b7513ad4ded884f6599b0dc6692
Source dataset
uspto-grants-1991_09
Patent number
US05051427

Reaction notes

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