Water → HCID 15729149, compound

HRID 1656946Notes

Reaction equation

HRID 1656946 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[Cl-].[NH4+].O.O1CCCC1>C(O)C.[Fe]>[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 251939N-(5-((4-(Hydroxy(oxido)amino)phenyl)thio)-1,3-thiazol-2-yl)acetamide

Product 1

HCID 15729149HCID 15729149, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-acetylamino-5-(4-nitrophenylthio)thiazole (2.8 g) and ammonium chloride (0.3 g) in a mixture of ethanol (60 ml), water (30 ml) and tetrahydrofuran (20 ml) was portionwise added the iron powder (3 g) at 80° C. with stirring. The mixture was refluxed for 2.5 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, washed with water and dried in vacuo to give 2-acetylamino-5-(4-aminophenylthio)thiazole (2.0 g, yield: 79.5%). mp: 255°-257° C. (dec.)

Workup

  1. temperatureThe mixture was refluxed for 2.5 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. customdried in vacuo

Sources & evidence

ORD record
ord-5c68793551164cc0a3944e500527a5cd
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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