Dicyclohexylcarbodiimide → 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide

HRID 2103084

反応式

HRID 2103084 の反応式
[C:1]1(=[CH:5][C:6]([OH:8])=O)[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[C:14]([C:16]=1[CH3:17])[NH2:15].CN(C)CCCN=C=NCC.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.C(N(CC)CC)C>[C:1]1(=[CH:5][C:6]([NH:15][C:14]2[CH:13]=[CH:12][C:11]([O:18][CH3:19])=[C:10]([CH3:9])[C:16]=2[CH3:17])=[O:8])[CH2:2][CH2:3][CH2:4]1

参加物

8

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 110948094-Methoxy-2,3-dimethylanilineHCID 219231732-Cyclobutylideneacetic acid

生成物 1

HCID 690533272-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide収率 65.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

Cyclobutylideneacetic acid (3.8 g), 5,6-dimethyl-4-methoxyaniline (5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (4.7 g), 1,3-dicyclohexylcarbodiimide (DCC) (2.4 g), 4-dimethylaminopyridine (DMAP) (805 mg) and triethylamine (TEA) (7.3 g) were dissolved in dichloromethane (80 mL). The mixture was stirred at room temperature overnight, concentrated, and the residue dissolved in ethyl acetate. The organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL), and a white solid was filtered out. The organic solution was then dried out by evaporation giving 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide as a brown solid (5.3 g). The product was used in the next step without further purification. MS: (m/z)=246 (100, M+H+).

後処理

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed with water (3×20 mL) and 1M HCl (3×20 mL)
  4. filtrationa white solid was filtered out
  5. customThe organic solution was then dried out by evaporation

出典と根拠

ORDレコード
ord-e76f5d88b4074044a32e6ad90da2d763
出典データセット
uspto-grants-2009_08
特許番号
US07576094B2

関連ノート

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