Bromine → N-{7-[bis-(4-methyl-benzyl)-amino]-4-methoxy-benzothiazol-2-yl}-benzamide

HRID 51863

反応式

HRID 51863 の反応式
[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]=1[O:36][CH3:37])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][N:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[C:17]2[C:18]3[S:11][C:10]([NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:12][C:13]=3[C:14]([O:36][CH3:37])=[CH:15][CH:16]=2)=[CH:34][CH:33]=1

参加物

5

反応物 2

HCID 24408BromineHCID 220157381-Benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea

生成物 1

HCID 22015745N-{7-[bis-(4-methyl-benzyl)-amino]-4-methoxy-benzothiazol-2-yl}-benzamide収率 58.3%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 500 mg (0.98 mmol) 1-benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea in 7 ml chloroform was added dropwise 0.050 ml (0.98 mmol) bromine and the reaction mixture heated at reflux for 18 hours. The mixture was then diluted with ethyl acetate and washed with water and then with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane) afforded 290 mg (58%) N-{7-[bis-(4-methyl-benzyl)-amino]-4-methoxy-benzothiazol-2-yl}-benzamide as a yellow solid. ES-MS m/e (%): 394 (M+Na+, 14), 508 (M+H+, 100).

後処理

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 18 hours
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9c17279ce9d6494aaa7c21c2479eadb7
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

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