Pyridine → HCID 18789704, compound

HRID 1106738Notes

Reaction equation

HRID 1106738 reaction equation
[CH3:1][C:2]1[C:11]([NH2:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][C:6]#[N:7].[CH3:14][S:15](Cl)(=[O:17])=[O:16].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:13][C:10]1[C:11]([NH:12][S:15]([CH3:14])(=[O:17])=[O:16])=[C:2]([CH3:1])[C:3]([O:4][CH2:5][C:6]#[N:7])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18789632HCID 18789632, compound

Product 1

HCID 18789704HCID 18789704, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of crude (2-methyl-3-amino-4-chlorophenoxy)acetonitrile (11.53 g) in toluene (PhMe) (60 mL) was added methanesulfonyl chloride (MsCl) (4.5 mL, 6.7 g) and the resultant solution was warmed to 35-40° C. Pyridine (py) (4.7 mL, 4.6 g) was then added slowly over 2 h. The resultant mixture was permitted to cool to ambient temperture and stirred for 24 h. The crude product mixture was then partitioned between 1N hydrochloric acid (100 mL), and a mixture of ethyl acetate (300 mL) and tetrahydrofuran (100 mL). The organic phase was washed with water, then concentrated to ca. 200 mL, leading to crystallization of the desired product. The white crystalline product was collected, rinsed with toluene, and dried to afford 10.40 g (65.1% yield) of N-(6-chloro-3-cyanomethoxy-2-methylphenyl)-methanesulfonamide (>97% pure by HPLC). This material could optionally be recrystallized from isopropanol.

Workup

  1. temperatureto cool to ambient temperture
  2. customThe crude product mixture was then partitioned between 1N hydrochloric acid (100 mL)
  3. additiona mixture of ethyl acetate (300 mL) and tetrahydrofuran (100 mL)
  4. washThe organic phase was washed with water
  5. concentrationconcentrated to ca. 200 mL
  6. customleading to crystallization of the desired product
  7. customThe white crystalline product was collected
  8. washrinsed with toluene
  9. customdried

Sources & evidence

ORD record
ord-6acc7f38e6244c61abf6b48fa58b2290
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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