Pyridine → beta-(N-chloroacetyl-2,6-dimethylphenylamino)propionaldehyde

HRID 46577

Reaction equation

HRID 46577 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(O[CH:9]([O:12]CC)[CH2:10][CH3:11])C.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]1(C)C=CC(S(O)(=O)=O)=C[CH:22]=1.[C:32](OCC)(=O)C>O.ClCCl.CC(C)=O>[Cl:1][CH2:2][C:3]([N:15]([C:20]1[C:19]([CH3:32])=[CH:18][CH:17]=[CH:16][C:21]=1[CH3:22])[CH2:11][CH2:10][CH:9]=[O:12])=[O:4]

Participants

9

Reactant 5

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 20858Propane, 1,1-diethoxy-

Product 1

HCID 20543839beta-(N-chloroacetyl-2,6-dimethylphenylamino)propionaldehyde

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

An 8.6-g (0.076-mol) sample of chloroacetyl chloride was added dropwise to a solution of 16 g (0.06 mol) beta-2,6-dimethylphenylamino)propionaldehyde diethylacetal and 6 g (0.076 mol) pyridine in 60 ml ethyl acetate. A salt immediately precipitated. The reaction mixture was stirred at about 25° C. for about 18 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give an oil. The oil was mixed with 100 ml acetone, 25 ml water and about 0.5 g p-toluenesulfonic acid. The resulting solution was stirred for 2 hours at 25° C., diluted with water, and extracted with ethyl ether. The ether extracts were evaporated to give a pale yellow oil. The yellow oil was dissolved in dichloromethane, dried over magnesium sulfate, treated with silica, filtered and evaporated to give 12.3 g of an oil which partially crystallized to give the product. Infrared analysis showed amide carbonyl absorption at 6.0 micron and aldehyde carbonyl absorption at 5.8 micron. The product is tabulated in Table I as Compound No. 13-A.

Workup

  1. customA salt immediately precipitated
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customto give an oil
  5. stirringThe resulting solution was stirred for 2 hours at 25° C.
  6. extractionextracted with ethyl ether
  7. customThe ether extracts were evaporated
  8. customto give a pale yellow oil
  9. dry with materialdried over magnesium sulfate
  10. additiontreated with silica
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-8e5ba7d470514b24a3b558424327f84c
Source dataset
uspto-grants-1979_11
Patent number
US04174210

Linked notes

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