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Triethylamine → Diethyl 1-(2,4-dimethoxy-benzyl)-3-ethyl-4-oxo-2,2-azetidinedicarboxylate

HRID 279785
ノート
印刷プレビュー

反応式

HRID 279785 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.Br[CH:32]([CH2:36][CH3:37])[C:33](Cl)=[O:34]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:33](=[O:34])[CH:32]([CH2:36][CH3:37])[C:7]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 907342-Bromobutanoyl chlorideHCID 13422978Diethyl {[(2,4-dimethoxyphenyl)methyl]amino}propanedioate

生成物 1

HCID 14211458Diethyl 1-(2,4-dimethoxy-benzyl)-3-ethyl-4-oxo-2,2-azetidinedicarboxylate収率 87%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

30 g (0.092 mole) of diethyl N-(2,4-dimethoxybenzyl)-amino-malonate prepared according to paragraph (b) of Example 1 are dissolved in a mixture of 90 ml of benzene and 15.6 ml (11.2 g, 0.111 mole) of triethyl amine and thereafter 20.5 g (0.111 mole) of 2-bromo butyric acid chloride are added dropwise under external ice-cooling. The reaction mixture is stirred under cooling for half an hour and thereafter at room temperature for half an hour. The precipitated crystalline substance is filtered off and washed twice with 20 ml of benzene. To the combined benzene mother liquor 31.2 g (22.4 g, 0.222 mole) of triethyl amine are added and the mixture is boiled for 6 hours. The precipitated crystalline substance is cooled and filtered. The mother liquor is extracted successively with 100 ml of water, twice with 100 ml of diluted hydrochloric acid each (a mixture of 90 ml of water and 10 ml of hydrochloric acid) and twice with 100 ml of water each. The organic layer is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated. The residual oil is made crystalline by rubbing with petrolether. Thus 31.5 g of diethyl 1-(2,4-dimethoxy-benzyl)-3-ethyl-4-oxo-2,2-azetidinedicarboxylate are obtained. M.p.: 69° C. (from a mixture of benzene and petrolether).

後処理

  1. temperaturecooling
  2. temperatureunder cooling for half an hour
  3. waitat room temperature for half an hour
  4. filtrationThe precipitated crystalline substance is filtered off
  5. washwashed twice with 20 ml of benzene
  6. temperatureThe precipitated crystalline substance is cooled
  7. filtrationfiltered
  8. extractionThe mother liquor is extracted successively with 100 ml of water, twice with 100 ml of diluted hydrochloric acid each (
  9. additiona mixture of 90 ml of water and 10 ml of hydrochloric acid) and twice with 100 ml of water each
  10. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated

出典と根拠

ORDレコード
ord-ef56fc614469493980ecb21ca6444981
出典データセット
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04587049

反応ノート

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