4-Methylmorpholine → Benzenemethanesulfonamide

HRID 849166Notes

Reaction equation

HRID 849166 reaction equation
C[N:2]1CCOCC1.[C:8]1([CH2:14][S:15](Cl)(=[O:17])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C>[CH2:14]([S:15]([NH2:2])(=[O:17])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 79724-MethylmorpholineHCID 74740Phenylmethanesulfonyl chloride

Product 1

HCID 78318BenzenemethanesulfonamideYield 118.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5 (7.54 g, 0.0298 mole; see Example 5) and 4-methylmorpholine (9.04 g, 0.0894 mole, 9.83 mL) in 300 mL of anhydrous acetonitrile at 0° C. under N2 was added α-toluene-sulfonyl chloride (11.36 g, 0.0596 mole) in one portion. The solution was stirred at 0° C. for 1 hour and allowed to warm to and stir at ambient temperature for 19 hours. The solution was filtered and evaporated. The crude residue was purified by flash chromatography on silica gel using a hexane, CH2Cl2 : 4,1 to CH2C12 gradient system and afforded 12.05 g (99% yield) of product 6 as waxy reddish solid, mp 62-63° C. TLC (silica; CH2Cl2), Rf=0.45.

Workup

  1. temperatureto warm to and
  2. stirringstir at ambient temperature for 19 hours
  3. filtrationThe solution was filtered
  4. customevaporated
  5. customThe crude residue was purified by flash chromatography on silica gel using a hexane, CH2Cl2

Sources & evidence

ORD record
ord-8fce61699fc249208c63dff5088213cc
Source dataset
uspto-grants-2000_01
Patent number
US06011047

Reaction notes

Loading…