Pyridine → 5-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

HRID 2308466ノート

反応式

HRID 2308466 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:10]([Br:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:5]=2[N:6]=1.N1C=CC=CC=1.[CH3:20][C:21]1[S:25][C:24]([C:26](Cl)=[O:27])=[CH:23][CH:22]=1>ClCCl>[Br:11][C:10]1[C:4]2[S:3][C:2]([NH:1][C:26]([C:24]3[S:25][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:27])=[N:6][C:5]=2[C:7]([O:12][CH3:13])=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 222832007-Bromo-4-methoxy-1,3-benzothiazol-2-amine

生成物 1

HCID 865849105-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Amino-7-bromo-4-methoxybenzothiazol (2.33 g, 9 mmol) is dissolved in dichloromethane (100 ml) and at 0° C. treated with pyridine (2.2 ml, 27 mmol) and 5-methyl-thiophene-2-carbonyl chloride (2.2 g, 13.5 mmol). The reaction mixture is allowed to warm to room temperature and after stirring for additional 18 h quenched with water (100 ml). After separation of the phases, the aqueous phases are extracted twice with ethyl acetate. The combined organic layers are then washed with brine, dried and avaporated to dryness. Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate affords the product as off-white solid. (34 mg, 69%). MS: m/e=384 (M+).

後処理

  1. customquenched with water (100 ml)
  2. customAfter separation of the phases
  3. extractionthe aqueous phases are extracted twice with ethyl acetate
  4. washThe combined organic layers are then washed with brine
  5. customdried
  6. customFlash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-8b65a03d0e7840c781f37db88e0ef02b
出典データセット
uspto-grants-2004_12
特許番号
US06835732B2

反応ノート

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