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

HRID 1886943Notes

Reaction equation

HRID 1886943 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-92cee1e69dff4d2c816103ea4cdda82f
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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