1-Chloro-2-nitrobenzene → 2-[(2-Nitrophenyl)sulfanyl]-1H-imidazole

HRID 1074202ノート

反応式

HRID 1074202 の反応式
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].C[O-].[Na+]>C(O)C>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1)([O-:16])=[O:15]

参加物

5

反応物 3

HCID 69451-Chloro-2-nitrobenzene2 回HCID 10942334Sodium MethoxideHCID 178527877HCID 178527877、化合物

生成物 1

HCID 131782532-[(2-Nitrophenyl)sulfanyl]-1H-imidazole収率 75%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 5.0 g (0.05 mole) of 2-mercaptoimidazole. 7.9 g (0.05 mole) of 2-chloronitrobenzene, 6.5 g (0.12 mole) of sodium methoxide and 150 ml of ethanol was stirred and refluxed for 5 hours. An additional 0.8 g of 2-chloronitrobenzene, was added and refluxing continued for 5 more hours. The mixture was filtered hot and the filtrates concentrated. The residue was partitioned with water and dichloromethane. The undissolved solid was collected by filtration to give 8.3 g of product. The dichloromethane was dried and concentrated. The residue was recrystallized from dichloromethane to give an additional 1.2 g of product. The total yield was 87% and the product was obtained as yellow rods, mp 178°-181° C.

後処理

  1. temperaturerefluxed for 5 hours
  2. temperaturerefluxing
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrates concentrated
  5. customThe residue was partitioned with water and dichloromethane
  6. filtrationThe undissolved solid was collected by filtration

出典と根拠

ORDレコード
ord-bf4a1a1db1ca420fa00ba27b55179cc2
出典データセット
uspto-grants-1990_11
特許番号
US04973599

反応ノート

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