Methanesulfonyl chloride → HCID 18615144, compound

HRID 635422Notes

Reaction equation

HRID 635422 reaction equation
[NH2:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CO.C(Cl)(Cl)Cl>[CH3:12][O:11][C:3]1[C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15579444HCID 15579444, compound

Product 1

HCID 18615144HCID 18615144, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

According to the method reported by A. A. Larsen in J. Med. Chem., 10, 462-472 (1967), the above compound was produced from Intermediate 66 (1.59 g) and methanesulfonyl chloride (750 μl). Here, however, the following alteration was incorporated in the purification step from the reaction mixture. Thus, the reaction was terminated with water (50 ml) and the mixture was agitated for 12 hours before extraction with ethyl acetate (once with 50 ml and twice with each 30 ml) with subsequent washing with 1 N hydrochloric acid (twice with each 25 ml) and with saturated aqueous sodium chloride solution, succesively, followed by distilling off of the solvent under a reduced pressure, whereby the above-identified compound was obtained (1.93 g). Rf=0.55 (methanol/chloroform of 1/19).

Workup

  1. customHere, however, the following alteration was incorporated in the purification step from the reaction mixture
  2. customThus, the reaction was terminated with water (50 ml)
  3. washtwice with each 30 ml) with subsequent washing with 1 N hydrochloric acid (twice with each 25 ml) and with saturated aqueous sodium chloride solution
  4. distillationby distilling off of the solvent under a reduced pressure, whereby the above-identified compound
  5. customwas obtained (1.93 g)

Sources & evidence

ORD record
ord-6cbc6c7f8de84c3283614f458787d1bb
Source dataset
uspto-grants-2001_02
Patent number
US06187809B1

Reaction notes

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