Methanesulfonyl chloride → HCID 12069574, compound

HRID 1716346Notes

Reaction equation

HRID 1716346 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[NH2:6][C:7]1[C:8]([CH3:29])=[C:9]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=2)=[O:17])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2>N1C=CC=CC=1>[CH3:28][O:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[C:16]([C:9]1[N:10]2[C:15]([CH:14]=[CH:13][CH:12]=[CH:11]2)=[C:7]([NH:6][S:1]([CH3:4])(=[O:3])=[O:2])[C:8]=1[CH3:29])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12069573HCID 12069573, compound

Product 1

HCID 12069574HCID 12069574, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.292 ml (3.78 mmol) of mesyl chloride is added to a solution of 350 mg (1.08 mmol) of the compound of Example 29 in 3 ml of pyridine, and the medium is stirred at room temperature for 4 hours. The reaction medium is concentrated under reduced pressure. The residue is taken up in 1 N hydrochloric acid and extracted with dichloromethane. The organic phase is separated after settling out, washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The residue is crystallized from ethanol. 327 mg of yellow crystals are obtained.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. customThe organic phase is separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-6e09a75e2d15451b99ed9e96d1dc9b5a
Source dataset
uspto-grants-2010_09
Patent number
US07803811B2

Reaction notes

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