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

HRID 51843

反応式

HRID 51843 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a841510e466244a7a8f6cd35137249f7
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

関連ノート

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