Water → HCID 15729155, compound

HRID 1656956Notes

Reaction equation

HRID 1656956 reaction equation
[C:1]([NH:5][C:6]1[S:7][C:8]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:9][N:10]=1)(=[O:4])[CH2:2][CH3:3].[Cl-].[NH4+].O.O1CCCC1>C(O)C.[Fe]>[C:1]([NH:5][C:6]1[S:7][C:8]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[CH:9][N:10]=1)(=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 15729154HCID 15729154, compound

Product 1

HCID 15729155HCID 15729155, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-propionylamino-5-(4-nitrophenylthio)thiazole (3 g), and ammonium chloride (1 g) in a mixture of ethanol (100 ml), water (30 ml) and tetrahydrofuran (70 ml) was portionwise added the iron powder at 80° C. with stirring. The mixture was refluxed for 2 hours with stirring. The reaction mixture was filtered by suction and the filtrate was concentrated under reduced pressure. The residue was triturated with water, the precipitates were collected by filtration and washed with water to give solid. The solid was recrystallized from ethanol to give 2-propionylamino-5-(4-aminophenylthio)thiazole (2.6 g, yield: 96.3%). mp: 185°-187° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. stirringwith stirring
  3. filtrationThe reaction mixture was filtered by suction
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was triturated with water
  6. filtrationthe precipitates were collected by filtration
  7. washwashed with water
  8. customto give solid
  9. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d49fde831a084a8b91ba24ffcc2c4eb6
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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