Sodium Bicarbonate → HCID 178495897, 화합물

HRID 69756

반응식

HRID 69756 반응식
[OH:1][N:2]=[C:3](Cl)[C:4]1[C:8]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[N:7][O:6][N:5]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[F:23])[NH2:19].C(=O)(O)[O-].[Na+]>O>[Br:15][C:16]1[CH:17]=[C:18]([NH:19][C:3]([C:4]2[C:8]([NH:9][CH2:10][CH2:11][O:12][CH3:13])=[N:7][O:6][N:5]=2)=[N:2][OH:1])[CH:20]=[CH:21][C:22]=1[F:23]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 27792863-Bromo-4-fluoroaniline2회HCID 136330165N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride

생성물 1

HCID 178495897HCID 178495897, 화합물수율 98.6%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
60 °C

실험 절차

N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride (46.0 g, 0.208 mol) was mixed with water (300 mL). The mixture was heated to 60° C. 3-Bromo-4-fluoroaniline [Oakwood products, product #013091] (43.6 g, 0.229 mol) was added and stirred for 10 min. A warm sodium bicarbonate (26.3 g, 0.313 mol) solution (300 mL water) was added over 15 min. The reaction was stirred at 60° C. for 20 min. LCMS indicated reaction completion. The reaction solution was cooled to room temperature and extracted with ethyl acetate (2×300 mL). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (76.7 g, 98%) as a crude brown solid. LCMS for C12H14BrFN5O3 (M+H)+: m/z=374.0, 376.0. 1H NMR (400 MHz, DMSO-d6): δ 11.55 (s, 1 H), 8.85 (s, 1 H), 7.16 (t, J=8.8 Hz, 1 H), 7.08 (dd, J=6.1, 2.7 Hz, 1 H), 6.75 (m, 1 H), 6.14 (t, J=5.8 Hz, 1 H), 3.48 (t, J=5.2 Hz, 2 H), 3.35 (dd, J=10.8, 5.6 Hz, 2 H), 3.22 (s, 3 H).

후처리

  1. stirringThe reaction was stirred at 60° C. for 20 min
  2. customreaction completion
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionextracted with ethyl acetate (2×300 mL)
  5. dry with materialThe combined ethyl acetate solution was dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-13afa7d229304102b581068b140fd63f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822511B2

연결된 노트

불러오는 중…