Ammonium Chloride → 2-p-Tolylbenzo[d]thiazol-5-amine

HRID 1886944Notes

Reaction equation

HRID 1886944 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:19]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:15]1([CH3:18])[CH:14]=[CH:13][C:12]([C:10]2[S:11][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:19][C:8]=3[N:9]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 221533055-Nitro-2-p-tolylbenzo[d]thiazole

Product 1

HCID 673310502-p-Tolylbenzo[d]thiazol-5-amineYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Nitro-2-p-tolylbenzo[d]thiazole (400 mg, 1.48 mmol) was suspended in ethanol/water (8 mL/4 mL) and heated at 80° C. Ammonium chloride (160 mg, 2.96 mmol) and iron powder (414 mg, 7.40 mmol) were added to the suspension, and the mixture was left stirring at 80° C. for 75 min. After cooling, the solution was filtrated through a pad of Celite® and the pad washed with ethanol. Water was added to the filtrate, ethanol was evaporated and the remaining aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 220 mg (62%) of the title compound (LCMS RT=6.51 min, MH+ 241.0)

Workup

  1. waitthe mixture was left
  2. temperatureAfter cooling
  3. filtrationthe solution was filtrated through a pad of Celite®
  4. washthe pad washed with ethanol
  5. additionWater was added to the filtrate, ethanol
  6. customwas evaporated
  7. extractionthe remaining aqueous layer was extracted with ethyl acetate
  8. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-3883e08e0f2741ff87742a26a00c7b7f
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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