Pyridine → HCID 18789704, compound

HRID 618231Notes

Reaction equation

HRID 618231 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 64.7%

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 temperature 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% field) of N-(6-chloro-3-cyanomethoxy-2-methylphenyl)-methanesulfonamide (>97% pure by HPLC). This material could optionally be recrystallized from isopropanol.

Workup

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

Sources & evidence

ORD record
ord-183678cfc1394fe1a41046f94ddea0c2
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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