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

HRID 963652

反応式

HRID 963652 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18fc9b6dbc484a6e8834325bb1a74df5
出典データセット
uspto-grants-1998_06
特許番号
US05763615

関連ノート

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