Propylenediamine → Ammonia

HRID 46163

반응식

HRID 46163 반응식
Cl.CO[C:4](=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:12][CH2:13][CH:14]([NH2:16])[CH3:15]>CO>[NH3:11].[CH3:15][CH:14]1[CH2:13][NH:12][C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:16]1

참가 물질

5

반응물 2

HCID 6567PropylenediamineHCID 5743287Methyl benzimidate hydrochloride

생성물 2

HCID 222AmmoniaHCID 135889848CID 135889848

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of benzimidic acid methyl ester hydrochloride (1 g) in MeOH (25 ml) was added 1,2-diaminopropane (545 μL) then the mixture was heated to reflux. After 16 h the mixture was cooled to room temperature and concentrated. The residue was taken up in MeOH then passed through Dowex 1×2-400 ion exchange resin (prewashed with 1M NaOH, H2O, MeOH) washing with MeOH. The filtrate was concentrated. Flash column chromatography (gradient, 0-10% MeOH/CHCl3 saturated with NH3) gave 4-methyl-2-phenyl-4,5-dihydro-1H-imidazole as a white solid (1.04 g) which was sufficiently pure for use in the next step. 1H-NMR (400 MHz, CDCl3) δ 7.84 (m, 2 H), 7.55-7.38 (m, 3 H), 4.16 (m, 1 H), 3.95 (dd, J=9.98 and 1.83 Hz, 1 H), 3.40 (m, 1 H), 1.32 (d, J=6.41 Hz, 3 H).

후처리

  1. temperaturethe mixture was heated to reflux
  2. concentrationconcentrated
  3. washwashing with MeOH
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-21c609ff16ee4fa194dce5b19780aaa0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541595B2

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