Acetaldehyde → N-[1-[(4-Methylphenyl)sulfonyl]ethyl]formamide

HRID 1159979Notes

Reaction equation

HRID 1159979 reaction equation
[CH:1]([NH2:3])=[O:2].[CH:4](=O)[CH3:5].C[Si](Cl)(C)C.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](O)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(OC(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C(#N)C>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH:4]([NH:3][CH:1]=[O:2])[CH3:5])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 713FormamideHCID 6101p-Toluenesulfonic acidHCID 6397ChlorotrimethylsilaneHCID 22541Di-tert-butyl ether

Product 1

HCID 4019666N-[1-[(4-Methylphenyl)sulfonyl]ethyl]formamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
-30 °C

Procedure

A stirred mixture of dry acetonitrile (500 mL) and dry toluene (500 mL) was cooled to −30° C., followed by the addition of formamide (50.7 g, 1.1 mol), acetaldehyde (37 g, 0.85 mol) and TMSCl (106.4 g, 0.98 mol) at −30° C. under N2 atmosphere. The reaction mixture was stirred at rt for 1 h and warmed to 55° C., then p-toluene sulphonic acid was added and stirred the reaction mixture at this temperature overnight. The reaction mixture was cooled to 0° C. and followed by the addition of 300 mL of tert-butyl ether and stirred for 1 h. The white precipitate formed was filtered off and dried. The crude product was taken into next step without further purification. Yield (crude): 110 g.

Workup

  1. temperaturewarmed to 55° C.
  2. stirringstirred the reaction mixture at this temperature overnight
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. stirringstirred for 1 h
  5. customThe white precipitate formed
  6. filtrationwas filtered off
  7. customdried
  8. customThe crude product was taken into next step without further purification
  9. customYield (crude)

Sources & evidence

ORD record
ord-2cfe520c962046219f82d67145039f18
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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