Sodium Hydroxide → 2-(beta-Cyanoethylaminocarbonyl)-4'-methylbiphenyl

HRID 620439노트

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HRID 620439 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].C(O)(=O)/C=C/C(O)=O.[NH2:31][CH2:32][CH2:33][C:34]#[N:35]>O.C(Cl)(Cl)Cl>[C:32]([CH2:33][CH2:34][NH:35][C:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)=[O:16])#[N:31]

참가 물질

7

반응물 4

HCID 14798Sodium Hydroxide2회HCID 24386Thionyl ChlorideHCID 815682-(4-Methylphenyl)benzoic acidHCID 6433176Propanenitrile, 3-amino-, (2E)-2-butenedioate (1:1)

생성물 1

HCID 144256702-(beta-Cyanoethylaminocarbonyl)-4'-methylbiphenyl수율 85.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

4'-methylbiphenyl-2-carboxylic acid (50.00 g, 0.236 mol,), thionyl chloride (87.5 ml, 1.20 mol) and chloroform (500 ml) were mixed and refluxed for 4 hours. The thionyl chloride and solvent were removed in vacuo, and the residue suspended in toluene (300 ml). The mixture was evaporated in vacuo and the residue suspended once more in toluene and evaporated to insure removal of traces of thionyl chloride. The resultant acid chloride was dissolved in tetrahydrofuran (100 ml) and slowly added in five equal portions alternatingly with five equal portions of 1.0N NaOH (236.0 ml, 0.236 mol) to a solution of β-aminopropionitrile fumarate (30.3 g, 0.236 mol) in 1.0 N NaOH (236.0 ml, 0.236 mol) at 0° with stirring. The reaction was allowed to warm slowly to room temperature. After 24 hrs, water (500 ml) was added and the aqueous mixture extracted with ethyl acetate (3×500 ml). The organic layers were combined and dried (MgSO4), and the solvent removed in vacuo to yield a crude solid which, after recrystallization from methylcyclohexane/butyl chloride, yielded 53.5 g of a white solid. M.P.=102.0°-103.5°. NMR (200 MHz, CDCl3) δ: 7.68 (d, 1H, J=7Hz); 7.56-7.19 (m, 7H); 5.65 (bm, 1H); 3.43 (d of t, 2H); 2.39 (t, 2H, J=7Hz). Anal. calcd. for C17H16N2O; C, 77.25; H, 6.10; N, 10.60. Found: C, 77.42; H, 6.40; N, 10.68.

후처리

  1. temperaturerefluxed for 4 hours
  2. customThe thionyl chloride and solvent were removed in vacuo
  3. customThe mixture was evaporated in vacuo
  4. customevaporated
  5. customremoval of traces of thionyl chloride
  6. dissolutionThe resultant acid chloride was dissolved in tetrahydrofuran (100 ml)
  7. extractionthe aqueous mixture extracted with ethyl acetate (3×500 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customto yield a crude solid which
  11. customafter recrystallization from methylcyclohexane/butyl chloride

출처 및 근거

ORD 기록
ord-ada02967fea043859132c8a6a7d81457
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820843

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