Methanesulfonyl chloride → HCID 14800671, compound

HRID 2073876Notes

Reaction equation

HRID 2073876 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 wter and extracted with ethyl acetate. The ethyl acetate extract is dried (magnesium sulfate) then applied to a silica gel column. The product is isolated be elution with the appropriate mixture of ethyl acetate and petroleum ether to obtain 3-(4-(2-quinolinylmethyloxy)benzyl)benzonitrile.

Workup

  1. additionThe reaction mixture is poured into ice wter
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialis dried (magnesium sulfate)
  5. customThe product is isolated
  6. washelution
  7. additionwith the appropriate mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-b3e6154d66de4ae19ea0dc916c4e9ba8
Source dataset
uspto-grants-1990_04
Patent number
US04920133

Reaction notes

Loading…