Hydrochloric Acid → 5-Nitro-2-p-tolylbenzo[d]thiazole

HRID 1896775

反応式

HRID 1896775 の反応式
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].[S].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[NH:24][C:25](=O)[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.Cl>C(O)C.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]2[S:10][C:25]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[N:24][C:16]=2[CH:17]=1)([O-:23])=[O:22]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 3330399N-(2-chloro-5-nitrophenyl)-4-methylbenzamideHCID 5362487Sulfur

生成物 1

HCID 221533055-Nitro-2-p-tolylbenzo[d]thiazole収率 43%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

Sodium sulfide nonahydrate (875 mg, 3.78 mmol) and sulfur (120 mg, 3.78 mmol) were heated until molten. The water was driven off with nitrogen to give a solid. The obtained solid was added in portions to N-(2-chloro-5-nitrophenyl)-4-methylbenzamide (1 g, 3.44 mmol) in ethanol (20 mL) at 85° C. The solution was stirred at 85° C. for 3 h. After cooling, 2M aqueous HCl was added, and the solution was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 10:90 v/v to afford 400 mg (43%) of the title compound.

後処理

  1. customto give a solid
  2. temperatureAfter cooling
  3. extractionthe solution was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated
  6. customThe resulting solid was purified by column chromatography
  7. washeluting with ethyl acetate/hexanes 10:90 v/v

出典と根拠

ORDレコード
ord-bd7746cd986c4eb88200fa943aeace55
出典データセット
uspto-grants-2013_08
特許番号
US08518980B2

関連ノート

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