Cyclohexylamine → N-Cyclohexyl-[2,1,3]-benzoxadiazole-5-carboxamide

HRID 1951019ノート

反応式

HRID 1951019 の反応式
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:15]1[O:16][N:17]=[C:18]2[CH:23]=[C:22]([C:24](Cl)=[O:25])[CH:21]=[CH:20][C:19]=12>ClCCl>[CH:1]1([NH:7][C:24]([C:22]2[CH:21]=[CH:20][C:19]3=[N:15][O:16][N:17]=[C:18]3[CH:23]=2)=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

生成物 1

HCID 25104041N-Cyclohexyl-[2,1,3]-benzoxadiazole-5-carboxamide収率 27%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of cyclohexylamine (1 ml) and triethylamine (1.7 ml) in dichloromethane (20 ml) was added a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (730 mg, 4 mmol) in dichloromethane (10 ml). After stirring the mixture for 1 hour, the organic phase was washed with 1N HCl and conc. NaHCO3 solution, dried over magnesium sulfate, and concentrated under vacuum. The residue was triturated with ether to give a white solid (265 mg, yield=27%). Mp=172-173° C., 1H NMR (300 MHz, CDCl3) δ 8.15 (s, 1H), 7.90 (d, 1H, J=9.0 Hz); 7.82 (d, J=9.0 Hz, 1H); 6.09 (“s”, NH, 1H), 4.05-3.97 (m, 1H) and 2.09-1.18 ppm (m, 10H).

後処理

  1. washthe organic phase was washed with 1N HCl and conc. NaHCO3 solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-4cba6b511d464615a7bff3f7fc4e3bbe
出典データセット
uspto-grants-2013_03
特許番号
US08404682B2

反応ノート

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