Acetaldehyde → HCID 57737178, compound

HRID 1157614Notes

Reaction equation

HRID 1157614 reaction equation
[CH:1]([NH2:3])=[O:2].[CH:4](=O)[CH3:5].[C:7]1(C)[CH:12]=[CH:11][C:10]([S:13]([OH:16])(=O)=[O:14])=[CH:9][CH:8]=1.C(OC(C)(C)C)(C)(C)C.C(#[N:29])C>C1(C)C=CC=CC=1>[NH2:29][C:8]1[CH:9]=[C:10]([S:13]([CH:4]([NH:3][CH:1]=[O:2])[CH3:5])(=[O:16])=[O:14])[CH:11]=[CH:12][CH:7]=1

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 713FormamideHCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 22541Di-tert-butyl ether

Product 1

HCID 57737178HCID 57737178, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 TMS-CI (106.4 g, 0.98 mol) at −30° C. under nitrogen atmosphere. The reaction mixture was stirred at rt for 1 h and warmed to 55° C., then para-toluene sulphonic acid was added and stirred the reaction mixture at this temperature overnight. The reaction mixture was cooled to 0° C., followed by the addition of tert-butyl ether (300 mL) and stirred for 1 h. The white precipitate formed was filtered off and dried. The crude product (110 g) was taken onto the next step without further purification.

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 (110 g) was taken onto the next step without further purification

Sources & evidence

ORD record
ord-3df567f45f204b5f9ebc5a33bcb619f6
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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