Bromine → 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

HRID 51843

반응식

HRID 51843 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])=[CH:5][C:4]=1[NH:15][C:16]([NH2:18])=[S:17].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([NH2:18])[S:17][C:5]=2[C:6]([N:9]([CH2:11][CH2:12][O:13][CH3:14])[CH3:10])=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 24408BromineHCID 22015743{2-Methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

생성물 1

HCID 220157444-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine수율 71%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a stirred solution of 1.40 g (5.20 mmol) {2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea in 35 ml chloroform was added dropwise 0.27 ml (5.27 mmol) bromine and the reaction mixture heated at reflux for 18 hours. The mixture was then cooled to room temperature, poured slowly onto sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 984 mg (71%) 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine as an orange crystalline solid. ES-MS m/e (%): 268 (M+H+, 100).

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 hours
  3. additionpoured slowly onto sodium bicarbonate solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a841510e466244a7a8f6cd35137249f7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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