1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-{(1E)-3-[(6-chlorohexyl)oxy]-3-oxoprop-1-enyl}phenyl 4-(2-methoxyethoxy)benzoate

HRID 523330ノート

反応式

HRID 523330 の反応式
Cl.CN(C)CCCN=C=NCC.[OH:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=[O:23])=[CH:16][CH:15]=1.[CH3:32][O:33][CH2:34][CH2:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:32][O:33][CH2:34][CH2:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([O:13][C:14]2[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])=[O:23])=[CH:18][CH:19]=2)=[O:42])=[CH:39][CH:38]=1

参加物

6

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64855624-(2-Methoxyethoxy)benzoic acidHCID 867326486-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate

生成物 1

HCID 867326494-{(1E)-3-[(6-chlorohexyl)oxy]-3-oxoprop-1-enyl}phenyl 4-(2-methoxyethoxy)benzoate収率 76.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

3 g (15 mmol) of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added to a solution of 3.1 g (15 mmol) of 6-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate, 0.186 g (1.5 mmol) of 4-dimethylaminopyridine in 70 mL of dichloromethane at 0° C. To this mixture, 5.1 g (15 mmol) of 4-(2-methoxyethoxy)benzoic acid in 40 mL of dichloromethane are added at 10° C. The solution is allowed to stir at room temperature for 22 hours. The reaction mixture is then partitioned between dichloromethane and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue using cyclohexane: ethylacetate 4:1 yielded 5.3 g (73%) of pure 4-{(1E)-3-[(6-chlorohexyl)oxy]-3-oxoprop-1-enyl}phenyl 4-(2-methoxyethoxy)benzoate as a white powder.

後処理

  1. customThe reaction mixture is then partitioned between dichloromethane and water
  2. washThe organic phase is washed repeatedly with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-0cdef7fd4d134af093d5932b33e027fd
出典データセット
uspto-grants-2016_05
特許番号
US09334366B2

反応ノート

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