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

HRID 443342

반응식

HRID 443342 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2009e095c37849a48698e9dd33264611
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04260410

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