Thiophene-3,4-diamine → 2-butyl-1H-thieno[3,4-d]imidazole

HRID 373608

반응식

HRID 373608 반응식
[NH2:1][C:2]1[C:6]([NH2:7])=[CH:5][S:4][CH:3]=1.Cl.[C:9](=N)(OCC)[CH2:10][CH2:11][CH2:12][CH3:13]>C(O)C>[CH2:10]([C:9]1[NH:1][C:2]2=[CH:3][S:4][CH:5]=[C:6]2[N:7]=1)[CH2:11][CH2:12][CH3:13]

참가 물질

4

반응물 2

HCID 643216Thiophene-3,4-diamineHCID 12283341Ethyl pentanimidate hydrochloride

생성물 1

HCID 193706342-butyl-1H-thieno[3,4-d]imidazole수율 78%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 3,4-diaminothiophene (116 mg, 1.01 mmol) and ethyl valeroimidate hydrochloride (504 mg, 3.05 mmol) in absolute ethanol (20 mL) was heated to reflux for 1 hour, cooled to room temperature and stirred for 15 hours. The mixture was concentrated and purified by flash chromatography (SiO2, 25% EtOAc/hexanes) to give 140 mg (78%) of 2-n-butyl-1H-thieno[3,4-d]imidazole as a tan solid: 1H NMR (300 MHz, CDCl3)δ 6.70 (s, 2H), 2.81 (t, 2H, J=7.5 Hz), 1.88-1.74 (m, 2H), 1.48-1.35 (m, 2H), 0.90 (t, 3H, J=7.2 Hz); FAB-MS: 181 (M+ +1).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe mixture was concentrated
  4. custompurified by flash chromatography (SiO2, 25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-9fef9ccd1d234b19a114beaf8724b3a2
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164407

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