Methanesulfonyl chloride → HCID 86601666, compound

HRID 916851Notes

Reaction equation

HRID 916851 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])=[CH:6][CH:5]=1.C(N(C(C)C)CC)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([C:16]#[N:17])[CH:14]=2)=[CH:21][CH:22]=1)(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68935235HCID 68935235, compound

Product 1

HCID 86601666HCID 86601666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-({2-[4-(2-hydroxyethyl)phenoxy]ethoxy}methyl)benzonitrile (5.04 g) and diisopropylethylamine (5.94 ml) in dichloromethane (50 ml) at 0° C. was added methanesulphonyl chloride (1.58 ml) dropwise and the mixture allowed to stir for 2 h. The resultant mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate. The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (6.02 g). LCMS RT=3.22 min.

Workup

  1. customThe resultant mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-779e7e53cd7045eea8215b1bb743b8fd
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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