Dichloromethane → HCID 3675686, compound

HRID 269436Notes

Reaction equation

HRID 269436 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6])[CH3:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.ClCCl>N1C=CC=CC=1>[CH3:2][O:1][C:3]1[CH:4]=[C:5]([NH:6][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 663013,5-Dimethoxyaniline

Product 1

HCID 3675686HCID 3675686, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3,5-dimethoxylaniline (24.0 g, 156.9 mmol) and p-toluenesulfonyl chloride (29.8 g, 156.9 mmol) in anhydrous pyridine (70 mL) was stirred and heated to reflux for 30 min under argon atmosphere. The reaction mixture was cooled to room temperature and poured into 400 mL of ice-cold water. Dichloromethane was added to extract the product. The organic layer was separated and washed with water, 5% HCl aqueous solution, water and brine and dried with anhydrous Na2SO4. Removal of solvent provided yellow solid crude, which was purified by re-crystallization in diethyl ether to afford 42.6 g (89.0%) of the title compound as light yellow crystalline solid. mp 103-104° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min under argon atmosphere
  3. extractionto extract the product
  4. customThe organic layer was separated
  5. washwashed with water, 5% HCl aqueous solution, water and brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customRemoval of solvent
  8. customprovided yellow solid crude, which
  9. customwas purified by re-crystallization in diethyl ether

Sources & evidence

ORD record
ord-0b55095825c444eabad43383b20d8943
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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