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

HRID 906669노트

반응식

HRID 906669 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c5705c1cd73a4237b853de80613792ce
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013003B2

반응 노트

불러오는 중…