Triethylamine → Triethylammonium bromide

HRID 536221

반응식

HRID 536221 반응식
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=1[NH2:8].[CH3:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].N#C[Br:24]>C(Cl)Cl>[CH3:14][O:13][C:9]1[C:7]2[N:8]=[C:16]([NH2:17])[N:3]3[CH2:4][CH2:5][N:1]=[C:2]3[C:6]=2[CH:12]=[CH:11][CH:10]=1.[N:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:15].[BrH:24]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 583773572-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxyaniline

생성물 2

HCID 2734074Triethylammonium bromide수율 296.1%HCID 178488375HCID 178488375, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
10 °C

실험 절차

2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methoxyaniline (Step 3, 22.0 g, 115 mmol) and Et3N (48.1 mL, 345 mmol) were dissolved in CH2Cl2 (200 mL), cooled to 10° C. in an ice bath and cyanogen bromide (24.4 g, 230 mmol) was added portionwise. A slight exotherm was noted, and the reaction was stirred overnight. The reaction was concentrated under reduced pressure, then treated with EtOAc (150 mL) and concentrated under reduced pressure again. Finally, the residue was treated with Heptane and concentrated under reduced pressure to give the title compound as a mixture with Et3N.HBr (62 g, 99%): HPLC MS RT=1.08 min, MH+=217.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.85 (3H, s), 4.09-4.16 (2H, m), 4.31-4.38 (2H, m), 7.23 (1H, t), 7.31 (1H, d), 7.57 (1H, dd).

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiontreated with EtOAc (150 mL)
  3. concentrationconcentrated under reduced pressure again
  4. additionFinally, the residue was treated with Heptane
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cbf1799c49494e7eaaac2cf948a53bb4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859572B2

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