Methanesulfonyl chloride → HCID 18789704, compound

HRID 1106722Notes

Reaction equation

HRID 1106722 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[O:5][CH2:6][C:7]#[N:8].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[Cl:12][C:11]1[C:2]([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])=[C:3]([CH3:13])[C:4]([O:5][CH2:6][C:7]#[N:8])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18789632HCID 18789632, compound

Product 1

HCID 18789704HCID 18789704, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3-amino-4-chloro-2-methylphenoxy)acetonitrile (4.76 g) was dissolved in pyridine (45 mL) under an atmosphere of nitrogen and cooled in an ice bath. Methanesulfonyl chloride (2.06 mL) was added dropwise, and then the mixture was allowed to stir overnight at room temperature. The reaction mixture was evaporated to dryness under reduced pressure to afford a residue which was flash chromatographed on silica and eluted with, first ethyl acetate:hexane (1:2), then with ethyl acetate: hexane (1:1) to afford 5.36 g as an 80:20 mixture of mono and bis mesylated product, respectively. This mixture was used in the next step without any further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture was evaporated to dryness under reduced pressure
  3. customto afford a residue which
  4. customchromatographed on silica
  5. washeluted with, first ethyl acetate:hexane (1:2)
  6. customwith ethyl acetate: hexane (1:1) to afford 5.36 g
  7. additionas an 80:20 mixture of mono and bis
  8. customThis mixture was used in the next step without any further purification

Sources & evidence

ORD record
ord-6b573a69b8cd4ea5b9223c91ecc854f9
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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