Triethylamine → 4-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylate

HRID 851942ノート

反応式

HRID 851942 の反応式
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[NH:11]1.C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([NH:7][C:8]([N:11]2[CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:17])[CH2:13][CH2:14][CH2:15][NH:10]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 184700714-Phenylbutyl perhydropyridazinecarboxylate

生成物 1

HCID 184700744-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylate収率 89.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Cyclohexylisocyanate (0.38 g, 3.0 mmol) was added to a CH2Cl2 solution containing 4-phenylbutyl perhydropyridazinecarboxylate (0.72 g, 2.75 mmol) and triethylamine (0.42 ml, 3 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere, and then diluted to 50 ml CH2Cl2. The organic layer was washed with water, dried, and concentrated. The crude material was purified by silica gel column to yield 0.95 g (89%) final product as clear oil. Rf=0.28 (2:1 hexane:EtOAc). 1H NMR (CDCl3, 400 MHz): δ 1.10 (m, 3H); 1.33 (m, 3H); 1.69 (m, 10H); 1.88 (m, 2H); 2.62 (m, 2H); 2.72 (m, 1H); 2.87 (m, 1H); 3.60 (m, 1H); 4.13 (m, 3H); 4.38 (m, 1H); 5.11 (d, 1H, J=8.3); 7.23 (m, 5H). Anal. Calcd. for C22H28N3O3-0.14H2O: C, 67.75; H, 8.60; N, 10.77. Found: C, 67.75; H, 8.45; N, 10.90.

後処理

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel column

出典と根拠

ORDレコード
ord-6a403b07fb864c96afab426ab9fad963
出典データセット
uspto-grants-2007_08
特許番号
US07253169B2

反応ノート

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