Acetonitrile → 2-Chloro-N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)benzamide

HRID 473987

反応式

HRID 473987 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9]([CH3:12])(=O)=O)[N:3]=1.[Cl:13][C:14]1[CH:29]=[CH:28][CH:27]=[CH:26][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23]C(S)=[CH:21][CH:20]=1)=[O:17].C(#N)C.C(N(CC)CC)C>O>[Cl:13][C:14]1[CH:29]=[CH:28][CH:27]=[CH:26][C:15]=1[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:12]([S:9][C:4]2[N:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[N:5]=2)=[CH:23][CH:24]=1)=[O:17]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidineHCID 271374192-chloro-N-(4-mercaptophenyl)benzamide

生成物 1

HCID 594207972-Chloro-N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)benzamide収率 74%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A 250 mL round bottom flask was charged with 4,6-dichloro-2-methanesulfonylpyrimidine (7.00 g, 26.6 mmol), 2-chloro-N-(4-mercapto-phenyl)-benzamide (6.33 g, 27.9 mmol) and acetonitrile (100 mL) under nitrogen. Once the solid had dissolved, the reaction mixture was cooled to 0° C. and triethylamine (3.7 mL, 26.6 mmol) was added dropwise. The solution was stirred at 0° C. for 10 min and then allowed to warm to room temperature and stirred for 1 h. After this time, water (50 mL) was added and a white solid precipitated and the reaction mixture stirred for an additional 4 h. After this time, the reaction mixture was filtered and the solid washed with acetonitrile (2×10 mL) to give the title compound as a white solid (8.03 g, 74%). 1H NMR (DMSO) 7.4-7.6 (5H, m), 7.7 (1H, s), 7.80-7.85 (2H, d), 10.9 (1H, s). MS (ES+): 412

後処理

  1. dissolutionOnce the solid had dissolved
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. customa white solid precipitated
  5. stirringthe reaction mixture stirred for an additional 4 h
  6. filtrationAfter this time, the reaction mixture was filtered
  7. washthe solid washed with acetonitrile (2×10 mL)

出典と根拠

ORDレコード
ord-943a771c3b424d38a34a58be5f016bfe
出典データセット
uspto-grants-2014_01
特許番号
US08637511B2

関連ノート

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