N-bromobutanimide → 2-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide

HRID 1508071노트

반응식

HRID 1508071 반응식
[CH3:1][N:2]([CH3:15])[S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:5])=[O:4].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[CH3:15][N:2]([CH3:1])[S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[C:12]([Br:23])[CH:13]=1)(=[O:4])=[O:5]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 589943702-(4-Amino-phenyl)-ethanesulfonic acid dimethylamide

생성물 1

HCID 589943492-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide수율 96.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of 737 mg (3.23 mmol) of 2-(4-amino-phenyl)-ethanesulfonic acid dimethylamide (as prepared in the previous step) in CH2Cl2 (20 mL) was cooled to 0° C. and treated with 574 mg (3.23 mmol) of NBS. The ice bath was removed and the mixture stirred at RT for 25 min. The mixture was diluted with CH2Cl2 (40 mL) and washed with saturated aqueous NaHCO3 (2×30 mL). The aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers were dried (MgSO4) and concentrated in vacuo to afford 955 mg (96%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 7.35 (d, 1H, J=2.0 Hz), 7.04 (dd, 1H, J=8.0, 2.0 Hz), 4.44 (br s, 2H), 3.21-3.14 (m, 2H), 2.96-2.89 (m, 2H), 2.84 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C10H15N2OSBr, 307.0/309.0 (M+H). found 307.0/309.0.

후처리

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with CH2Cl2 (40 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×30 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (1×30 mL) the combined organic layers
  5. dry with materialwere dried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-552b4eba91a748ee80e4122ac3e91fe1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221797B2

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