Methanesulfonyl chloride → HCID 18615144, compound

HRID 1636950Notes

Reaction equation

HRID 1636950 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, successively, 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-6456d89de89d442a8f93c902ea0ddade
Source dataset
uspto-grants-2000_03
Patent number
US06037362

Reaction notes

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