Methacryloyl chloride → N'-methacryloyl-ethylenediamine

HRID 1531336노트

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HRID 1531336 반응식
Cl.C[NH:3][CH2:4][CH2:5][NH2:6].[OH-].[Na+].[C:9](Cl)(=[O:13])[C:10]([CH3:12])=[CH2:11]>C(Cl)(Cl)Cl>[C:9]([NH:3][CH2:4][CH2:5][NH2:6])(=[O:13])[C:10]([CH3:12])=[CH2:11]

참가 물질

5

반응물 3

HCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 22641190HCID 22641190, 화합물

생성물 1

HCID 10154062N'-methacryloyl-ethylenediamine수율 127.2%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

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온도
0 °C

실험 절차

The intermediate N-t-BOC, N-methyl-ethylenediamine monohydrochloride prepared in example 5 (10 mmol, 2.1 g) was stirred with 2M NaOH (11 cm3) at room temperature for 10 min. The solution was then cooled to 0° C., and to this, was added a solution of methacryloyl chloride (11 mmol, 1.1 cm3) in chloroform (30 cm3), dropwise. After the addition was complete, the reaction mixture was stirred at 0° C. for a further 1 h. The organic and aqueous phases were then separated, and the aqueous phase extracted with chloroform. The organic extracts were combined, dried (MgSO4), filtered and conc. in vacuo, to give the crude product. The crude product was stirred at room temperature over a slurry of basic alumina in chloroform for 18 hr. Removal of the alumina and concentration of the filtrate then gave a pale yellow oil. Purification by flash chromatography (silica gel, diethyl ether: hexane : methanol elution) afforded N-t-BOC, N-methyl, N′-methacryloyl-ethylenediamine (Rf0.51) as a yellow oil (1.63 g, 67%). δH (400 MHz; CDCl3) 6.94 (1H, br s), HNOC(H3C)C═CHaHb; 5.74 (1H, br m), (H3C)C═CHaHb; 5.30 (1H, br m), (H3C)C═CHaHb; 3.43 (4H, br m), 2×CH2; 2.87 (3H, s), N(CH3); 1.93 (3H, br m), CH3; 1.44 (9H, s), C(CH3)3. δC (75.4 MHz; CDCl3) 168.52, NHOC(H3C)C═CH2; 157.33, NHCO2C(CH3)3; 139.36, (H3C)C═CH2; 119.81, (H3C)C═CH2; 80.85 C(CH3)3; 47.32, CH2N(CH3)OC(H3C)C═CH2; 39.32, CH2NHCO2C(CH3)3; 34.68, N(CH3); 28.33, C(CH3)3; 18.47, CH3. Found: (HM+.) 243.17178.

후처리

  1. additionAfter the addition
  2. customThe organic and aqueous phases were then separated
  3. extractionthe aqueous phase extracted with chloroform
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered and conc. in vacuo
  6. customto give the crude product
  7. customRemoval of the alumina and concentration of the filtrate
  8. customthen gave a pale yellow oil
  9. customPurification
  10. washby flash chromatography (silica gel, diethyl ether: hexane : methanol elution)

출처 및 근거

ORD 기록
ord-b11b0231aacb417a9c347b62a56a84de
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06197906B1

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