Hydrochloric Acid → 6-ethyl-N,N-dimethyl-2-methoxy-benzamide

HRID 22178ノート

反応式

HRID 22178 の反応式
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].CN(C)[CH2:16][CH2:17]N(C)C.C([Li])(CC)C.C(Br)C.Cl>C1CCCCC1.CCC(C)C.O.O1CCCC1>[CH2:16]([C:9]1[C:4]([C:3]([N:2]([CH3:1])[CH3:13])=[O:12])=[C:5]([O:10][CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:17]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 111596462-Methoxy-N,N-dimethylbenzamideHCID 178418400CID 53628100

生成物 1

HCID 199273926-ethyl-N,N-dimethyl-2-methoxy-benzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 19019564Cyclohexane isopentane溶媒

反応条件

温度
-70 °C

実験手順

39.5 g of N,N-dimethyl-2-methoxy-benzamide and 28.5 ml of tetramethylethylenediamine are introduced into 190 ml of absolute tetrahydrofuran and the mixture is lithiated at -70° C. with 150 ml of a 1.4-molar sec-butyllithium solution in cyclohexane/isopentane. After subsequently stirring at -70° C. for 45 minutes, 25.6 ml of ethyl bromide are added dropwise within 25 minutes and the reaction mixture is then allowed to warm slowly to room temperature. Water is then added and the mixture is adjusted to pH 2 with hydrochloric acid and extracted twice with diethyl ether. The residue is purified on silica gel using ethyl acetate/n-hexane (4:6) to yield 6-ethyl-N,N-dimethyl-2-methoxy-benzamide in the form of a colourless oil, 1H-NMR (CDCl3): 3.82 ppm (m), 3.40 ppm (m) and 3.12 ppm (2q, N(CH2CH3)2), 2.56 ppm (m, CH2CH3).

後処理

  1. temperatureto warm slowly to room temperature
  2. extractionextracted twice with diethyl ether
  3. customThe residue is purified on silica gel

出典と根拠

ORDレコード
ord-e236a500874a40a585bf4dcbacb3eccc
出典データセット
uspto-grants-1995_06
特許番号
US05428002

反応ノート

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