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

HRID 1886943

반응식

HRID 1886943 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-92cee1e69dff4d2c816103ea4cdda82f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501713B2

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