Methanesulfonyl chloride → Methansulfonic Acid 3-(benzhydrylidene-hydrazinocarbonyl)-2-(3-methoxy-phenyl)-propyl Ester

HRID 8202Notes

Reaction equation

HRID 8202 reaction equation
[C:1](=[N:14][NH:15][C:16](=[O:29])[CH2:17][CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH2:19][OH:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl>[C:1](=[N:14][NH:15][C:16]([CH2:17][CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH2:19][O:20][S:31]([CH3:30])(=[O:33])=[O:32])=[O:29])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 865926214-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

Product 1

HCID 86592622Methansulfonic Acid 3-(benzhydrylidene-hydrazinocarbonyl)-2-(3-methoxy-phenyl)-propyl Ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide and (1.7 g, 4.38 mmol) and 4-dimethylaminopyridine (26 mg, 0.22 mmol) in pyridine (15 mL) is cooled to 0° C. treated with methanesulfonyl chloride (0.4 mL, 5.25 mmol) and stirred 18 h at room temperature. The mixture is diluted with dichloromethane (30 mL) and washed with 1 N hydrochloric acid (30 mL), a saturated solution of sodium bicarbonate and brine. The mixture is dried over magnesium sulfate, filtered, concentrated in vacuo and chromatographed on SiO2 (2% methanol/dichloromethane) to yield the title compound, 1.64 g (80%), as yellow foam.

Workup

  1. washwashed with 1 N hydrochloric acid (30 mL)
  2. dry with materialThe mixture is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customchromatographed on SiO2 (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-1f77ff8a164647918c5589fae50e5da4
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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