Formamide → N-[(Toluene-4-sulfonyl)-(3-chloro-4,5-dimethoxyphenyl)methyl]formamide

HRID 874720Notes

Reaction equation

HRID 874720 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([S:20]([OH:22])=[O:21])=[CH:16][CH:15]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH:39]([NH2:41])=[O:40]>>[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([S:20]([CH:7]([C:6]2[CH:5]=[C:4]([O:10][CH3:11])[C:3]([O:12][CH3:13])=[C:2]([Cl:1])[CH:9]=2)[NH:41][CH:39]=[O:40])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 10818p-Toluenesulfinic acidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2400523-Chloro-4,5-dimethoxybenzaldehyde

Product 1

HCID 46938394N-[(Toluene-4-sulfonyl)-(3-chloro-4,5-dimethoxyphenyl)methyl]formamide

Conditions

Temperature
65 °C

Procedure

5-Chloroveratraldehyde (5.7 g, 23.4 mmol), para-toluenesulfinic acid (3.0 g, 19.3 mmol) and camphorsulfonic acid (110 mg, 0.47 mmol) were treated with formamide (10 mL). Upon heating to 65° C. the reaction mixture turned into a solution and after two hours the product began to precipitate. After stirring for 16 h the precipitate was filtered, washed with methanol and dried in vacuum.

Workup

  1. customto precipitate
  2. filtrationwas filtered
  3. washwashed with methanol
  4. customdried in vacuum

Sources & evidence

ORD record
ord-425d241388c24a97a7cc0acd27d72100
Source dataset
uspto-grants-2015_03
Patent number
US08980933B2

Reaction notes

Loading…