N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide → 4-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholine

HRID 1188778노트

반응식

HRID 1188778 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[C:5]([N+:15]([O-])=O)[C:4]=1[NH:18][C:19](=O)[CH3:20]>CC(O)=O.[Fe]>[CH3:1][O:2][C:3]1[C:4]2[N:18]=[C:19]([CH3:20])[NH:15][C:5]=2[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1

참가 물질

4

반응물 1

HCID 66977019N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide

생성물 1

HCID 669771484-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholine수율 100.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

To a refluxing solution of combined batches of N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide (2.06 g) in HOAc (60 mL) was added iron powder (1.18 g) and the mixture was stirred at reflux temperature overnight. It was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo and the residue was washed with EtOAc:petroleum ether=1:1 to afford crude product as a solid (1.73 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.56 (s, 3H), 3.12 (t, 4H, J=4.8 Hz), 3.88 (t, 4H, J=4.8 Hz), 3.94 (s, 3H), 6.39 (s, 1H), 6.62 (s, 1H); LC-MS: m/e=248 [M+1]+

후처리

  1. temperatureat reflux temperature overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in-vacuo
  4. washthe residue was washed with EtOAc

출처 및 근거

ORD 기록
ord-0cc34f4420f54b1e8b3443c73cb0afc5
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674090B2

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