Ammonia → 3-Bromo-5-methylbenzamide

HRID 657342

반응식

HRID 657342 반응식
C1N=C[N:3](C(N2C=NC=C2)=O)C=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:17](O)=[O:18].N>CC(=O)OCC>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:17]([NH2:3])=[O:18]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 34331273-Bromo-5-methylbenzoic acid

생성물 1

HCID 578133983-Bromo-5-methylbenzamide수율 94.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

CDI (42.2 g, 260.4 mmol) was cautiously added to a solution of 3-bromo-5-methylbenzoic acid (16.0 g, 74.4 mmol) in EA (300 mL), and then the mixture was kept at reflux for 3 h. After cooling to room temperature, NH3 (g) was passed though the mixture for 1 h. It was filtered and the organic layer was washed with HCl (10%, 100 mL) and water (100 mL). The organic phase was dried over Na2SO4 and concentrated in vacuum to obtain 15.0 g of 3-bromo-5-methylbenzamide as white crystals (yield: 94%). 1H NMR (400 MHz, CDCl3) δ 7.73-7.72 (m, 1H), 7.56-7.55 (m, 1H), 7.50-7.49 (m 1H), 2.39 (s, 3H).

후처리

  1. temperatureat reflux for 3 h
  2. filtrationIt was filtered
  3. washthe organic layer was washed with HCl (10%, 100 mL) and water (100 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-82bbc7aaf03a4f958a9b8417b76e89ce
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071588B2

연결된 노트

불러오는 중…