Dichloromethane → Benzenemethanesulfonamide

HRID 1532797Notes

Reaction equation

HRID 1532797 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(Cl)Cl>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

5

Reactant 3

HCID 6344DichloromethaneHCID 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 CH2Cl2 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
  2. stirringto and stir 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-59d3904ad3ec457bb765ef2cd49e68b0
Source dataset
uspto-grants-2001_03
Patent number
US06204384B1

Reaction notes

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