N,N'-Dimethylethylenediamine → 4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

HRID 76800

반응식

HRID 76800 반응식
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][C:19]1=[O:24].CNCCNC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([S:8][C:9]1[C:10]([CH2:16][CH3:17])=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2=[O:24])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 669533-MorpholinoneHCID 66911124Benzyl(3-bromo-2-ethylphenyl)sulfane

생성물 1

HCID 669111454-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

Intermediate 4 (1.075 g, 3.5 mmol), morpholin-3-one (389 mg, 3.85 mmol), CuI (67 mg, 0.35 mmol), N,N′-dimethylethylene diamine (75 μl, 0.7 mmol) and K2CO3 (1.064 g, 7.7 mmol) were suspended in toluene (30 ml) under argon and heated to 110° C. for 20 h. After cooling to RT the reaction mixture was quenched by addition of 100 ml sat. aq. NH4Cl, 150 ml concentrated NH3 in water and 100 ml water and extracted three times with ethyl acetate. The organic layers were combined and washed with water and sat. aq. NaCl-solution, dried with MgSO4, filtered and evaporated to dryness. The resulting oil crystallizes upon standing and was triturated with n-heptane-MTBE (19:1).

후처리

  1. temperatureAfter cooling to RT the reaction mixture
  2. customwas quenched by addition of 100 ml sat. aq. NH4Cl, 150 ml concentrated NH3 in water and 100 ml water
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and sat. aq. NaCl-solution
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting oil crystallizes
  9. customwas triturated with n-heptane-MTBE (19:1)

출처 및 근거

ORD 기록
ord-7ec6910c258a42a1b1e945b9df3675f2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835653B2

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