Dichloromethane → Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

HRID 1585952Notes

Reaction equation

HRID 1585952 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.C(Cl)Cl.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(C(C)C)CC)(C)C>C1COCC1>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:4]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH2:3][CH2:2][O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:11][CH:12]=1)#[N:15]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 187796904-(3-Hydroxy-1-imidazol-1-yl-propyl)-benzonitrile

Product 1

HCID 54062353Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-(3-hydroxy-1-imidazol-1-yl-propyl)-benzonitrile (1.4 gm, 6.16 mmol) was suspended in 2:1 methylene chloride: THF (100 mL) under argon and cooled to 0° C. in an ice bath. Methanesulfonylchloride (1 mL, 12.4 mmol) was added followed by diisopropylethylamine (3.22 mL, 18.5 mmol). The reaction was stirred for 4 hours and the solvent was removed in vacuo. The residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel using using 1:3 ethyl acatate: hexanes. The desired fractions were concentrated in vacuo to give the desired product.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel using
  5. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-7ec47d98df8649f48916f77bebdebe42
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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