2-(4-Isobutylphenyl)propiononitrile → HCID 178440852, 화합물

HRID 2242924

반응식

HRID 2242924 반응식
Cl.[NH2:2][OH:3].CC(C)([O-])C.[Na+].[CH2:10]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:23])[C:21]#[N:22])=[CH:16][CH:15]=1)[CH:11]([CH3:13])[CH3:12]>C(O)C>[CH2:10]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:23])[C:21]([NH:2][OH:3])=[NH:22])=[CH:18][CH:19]=1)[CH:11]([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 1083742-(4-Isobutylphenyl)propiononitrileHCID 443297Hydroxyamine hydrochlorideHCID 23676156Sodium t-butoxide

생성물 1

HCID 178440852HCID 178440852, 화합물수율 70%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A mixture of hydroxylamine hydrochloride (0.38 g, 5.32 mmol) and sodium tert-butoxide (0.5 g, 5.28 mmol) in ethyl alcohol (10 mL) is stirred at r.t. for 15′; the precipitate is filtered off and the mother liquors are added dropwise to a solution of 2-(4-isobutylphenyl)propionitrile (0.11 g, 0.49 mmol) in absolute ethyl alcohol (3 mL). The resulting solution is refluxed 18 h. After cooling at r.t. the solvents are evaporated under reduced pressure and the crude residue is diluted in trichloromethane (25 mL), washed with 5% solution of citric acid (2×15 mL), then with a saturated solution of NaCl (2×15 mL), dried over Na2SO4 and evaporated under vacuum to give 2-(4-isobutylphenyl)-N-hydroxy-propionamidine isolated as white solid after crystallisation from n-hexane (0.075 g, 0.34 mmol). Yield 70%. m.p. 75-78° C. 1H-NMR (CDCl3): δ 7.25 (d, 2H, J=7 Hz); 7.12 (d, 2H, J=7 Hz); 5.030 (bs, 1H, NH); 4.35 (bs, 2H, NH—OH); 3.58 (q, 1H, J=8 Hz); 2.48 (d, 2H, J=8 Hz); 1.87 (m, 1H); 1.50 (d, 3H, J=8 Hz); 0.92 (d, 6H, J=8 Hz).

후처리

  1. filtrationthe precipitate is filtered off
  2. temperatureThe resulting solution is refluxed 18 h
  3. temperatureAfter cooling at r.t. the solvents
  4. customare evaporated under reduced pressure
  5. additionthe crude residue is diluted in trichloromethane (25 mL)
  6. washwashed with 5% solution of citric acid (2×15 mL)
  7. dry with materialwith a saturated solution of NaCl (2×15 mL), dried over Na2SO4
  8. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-45b6f2ab10d4437c90f3c55c88cbef7e
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674806B2

연결된 노트

불러오는 중…