Pyridine → N-(3-cyanomethoxyphenyl)methanesulfonamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][C:7]#[N:8].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C1(C)C=CC=CC=1>[C:7]([CH2:6][O:5][C:4]1[CH:3]=[C:2]([NH:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH:11]=[CH:10][CH:9]=1)#[N:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a solution of crude (3-aminophenoxy)acetonitrile (ca 12.1 g) in toluene (50 mL) was added pyridine (6.6 mL) and methanesulfonyl chloride (6.3 mL) at 5° C. and the resultant mixture was warmed to ambient temperature. After 2 h, the crude product mixture was partitioned between 1N hydrochloric acid (100 mL) and ethyl acetate (100 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (50 mL). The combined organic solution was washed with water, then concentrated with concomitant replacement of solvent with isopropanol. After cooling the resultant mixture to 5° C., the white crystalline product was collected, rinsed with cold isopropanol, and dried to afford 12.14 g (65.1% yield based on cyanomethyl tosylate) of N-(3-cyanomethoxyphenyl)methanesulfonamide (99.8% pure by HPLC). This material could optionally be recrystallized from isopropanol.
Workup
- customthe crude product mixture was partitioned between 1N hydrochloric acid (100 mL) and ethyl acetate (100 mL)
- customThe phases were separated
- extractionthe aqueous phase extracted with ethyl acetate (50 mL)
- washThe combined organic solution was washed with water
- concentrationconcentrated with concomitant replacement of solvent with isopropanol
- customthe white crystalline product was collected
- washrinsed with cold isopropanol
- customdried
Sources & evidence
- ORD record
- ord-67dfdcacc3c0401bb37bb9be0dcd570b
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057349
Reaction notes
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