Ammonium Chloride → HCID 20186417, compound

HRID 2308942Notes

Reaction equation

HRID 2308942 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:18][CH2:17][C:16]3[CH:15]=[N:14][NH:13][C:12]=3[C:10]=2[CH:11]=1)([O-])=O>O.C(O)C.[Fe]>[NH2:3][C:6]1[CH:7]=[CH:8][C:9]2[S:18][CH2:17][C:16]3[CH:15]=[N:14][NH:13][C:12]=3[C:10]=2[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 20186437HCID 20186437, compound

Product 1

HCID 20186417HCID 20186417, compoundYield 65.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of iron powder (8.53 g) and ammonium chloride (0.85 g) in water (22 ml) and ethanol (66 ml) was added portionwise 8-nitro-1,4dihydro[1]benzothiopyrano[4,3-c]pyrazole (6.6 g) under reflux over a period of 15 minutes. After being stirred for 30 minutes under reflux, the mixture was filtered and the filtrate was evaporated in vacuo. To the residue were added aqueous sodium bicarbonate and ethyl acetate and the mixture was stirred at room temperature. The resulting precipitate was collected by filtration, washed with water, and recrystallized from a mixture of tetrahydrofuran and methanol to give 8-amino-1,4-dihydro[1]benzothiopyrano[4,3-c]pyrazole (3.79 g).

Workup

  1. temperatureunder reflux over a period of 15 minutes
  2. temperatureunder reflux
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. additionTo the residue were added aqueous sodium bicarbonate and ethyl acetate
  6. stirringthe mixture was stirred at room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water
  9. customrecrystallized from a mixture of tetrahydrofuran and methanol

Sources & evidence

ORD record
ord-f765b3498b114380bfa71af9b393ec36
Source dataset
uspto-grants-1987_09
Patent number
US04692444

Reaction notes

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