2-Amino-2-methyl-1-propanol → 2-(4-Ethylphenyl)-4,4-dimethyl-2-oxazoline

HRID 39627

반응식

HRID 39627 반응식
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH2:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=O)=[CH:11][CH:10]=1)[CH3:8].O=S(Cl)Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13]2[O:4][CH2:3][C:2]([CH3:6])([CH3:5])[N:1]=2)=[CH:11][CH:10]=1)[CH3:8]

참가 물질

6

반응물 4

HCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 853684-Ethylbenzoyl chloride

생성물 1

HCID 128725592-(4-Ethylphenyl)-4,4-dimethyl-2-oxazoline수율 98.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

To a 3-neck, 2 L round bottom flask was added 173.71 g (1.0 mol, 97%) of 2-amino-2-methyl-1-propanol in 300 mL of dry methylene chloride. The flask was equipped with a magnetic stir bar and thermometer and was placed into a dry ice/acetone bath and cooled to 0° C. From a separatory funnel, a solution of 4-ethylbenzoyl chloride (168.5 g, 1.0 mol), dissolved in about 300 mL of methylene chloride was slowly added, while maintaining the reaction temperature below 5° C. The mixture was allowed to stir at room temperature overnight. Solid propanol amine-HCl was filtered off and the filter cake was washed with methylene chloride. The combined methylene chloride extracts were concentrated partially on a rotary evaporator and used directly in the next step. The intermediate amide solution generated in the first step was cooled in an ice bath and DMF (0.5 mL) was added. 125 g (1.04 mol) of SOCl2 in 50 mL of methylene chloride from a separatory funnel was added drop-wise at a controlled rate, keeping the reaction temperature at 0.5° C. The reaction was stirred at room temperature for an additional 2-3 hours. The reaction mixture was cooled in an ice bath and 25% NaOH was added to make the aqueous layer basic (pH=11-12). The mixture was transferred to a large separatory funnel, the methylene chloride layer was separated, and the aqueous layer was extracted twice with chloroform. The combined organic phases were dried and evaporated to yield 201 g of 2-(4-ethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole as a yellow viscous oil. 1H NMR (CDCl3, 300 MHz), δ (ppm): 7.8 (d, 2H), 7.2 (d, 2H), 4.088 (s, 2H), 2.68 (q, 2H), 1.375 (s, 6H), 1.24 (t, 3H).

후처리

  1. customThe flask was equipped with a magnetic stir bar
  2. customthermometer and was placed into a dry ice/acetone bath
  3. additionwas slowly added
  4. temperaturewhile maintaining the reaction temperature below 5° C
  5. filtrationSolid propanol amine-HCl was filtered off
  6. washthe filter cake was washed with methylene chloride
  7. concentrationThe combined methylene chloride extracts were concentrated partially on a rotary evaporator
  8. temperaturewas cooled in an ice bath
  9. additionDMF (0.5 mL) was added
  10. customat 0.5° C
  11. stirringThe reaction was stirred at room temperature for an additional 2-3 hours
  12. temperatureThe reaction mixture was cooled in an ice bath
  13. customThe mixture was transferred to a large separatory funnel
  14. customthe methylene chloride layer was separated
  15. extractionthe aqueous layer was extracted twice with chloroform
  16. customThe combined organic phases were dried
  17. customevaporated

출처 및 근거

ORD 기록
ord-d0540e9edcc8411492c67d967cfebe1f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524948B2

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