Toluene → 2-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal

HRID 963652

반응식

HRID 963652 반응식
Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:19][O:20][CH:21]([O:25][CH3:26])[CH:22]([NH2:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CS(C)=O>[CH3:19][O:20][CH:21]([O:25][CH3:26])[CH:22]([NH:24][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH3:23]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 936582,2-Dimethoxy-1-methylethylamineHCID 8198614-(Benzyloxy)-2-chloro-1-nitrobenzene

생성물 1

HCID 190831162-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of benzyl 3-chloro-4-nitrophenyl ether (48.2 g, 0.183 mole), 2-aminopropionaldehyde dimethyl acetal (65.3 g, 0.55 mole), potassium carbonate (101 g, 0.73 mole) and toluene in dry dimethyl sulfoxide, under nitrogen, is stirred at 99°-105° C. for 20 hours, cooled to room temperature and filtered. The filter cake is washed with ether. The combined filtrates are mixed with ice water. The phases are separated and the aqueous phase is extracted with ether. The ether extracts are combined with the organic phase. The combined organic phase is washed with six portions of water, dried (Na2SO4) and concentrated in vacuo to give an oil residue which is crystallized in methanol to afford the title product as a yellow solid, 39.6 g (64.5%). A sample is recrystallized from methanol to afford a yellow solid, mp 57°-62° C., identified by elemental and NMR analyses.

후처리

  1. filtrationfiltered
  2. washThe filter cake is washed with ether
  3. additionThe combined filtrates are mixed with ice water
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ether
  6. washThe combined organic phase is washed with six portions of water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto give an oil residue which
  10. customis crystallized in methanol

출처 및 근거

ORD 기록
ord-18fc9b6dbc484a6e8834325bb1a74df5
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763615

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