Water → Thiazosulfone

HRID 1656937

Reaction equation

HRID 1656937 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:5][N:6]=1.[Cl-].[NH4+].O1CCCC1.O>C(O)C.[Fe]>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1535p-Nitrophenyl-2-aminothiazol-5-ylsulphoneHCID 8028TetrahydrofuranHCID 25517Ammonium Chloride

Product 1

HCID 10124ThiazosulfoneYield 86.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-amino-5-(4-nitrophenylsulfonyl)thiazole (4.0 g) and ammonium chloride in a mixture of ethanol (80 ml), tetrahydrofuran (40 ml) and water (30 ml) was portionwise added the iron powder (4 g) at 80° C. with stirring. The mixture was refluxed for 1.5 hours with stirring. The reaction mixture was filtered by suction and the filtrate was concentrated under reduced pressure. The residue was triturated with water and the precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-5-(4-aminophenylsulfonyl)thiazole (3.10 g, yield: 86.6%). mp: 218°-219° C. IR (Nujol): 3400, 3300, 1620, 1595, 1535, 1380 cm-1

Workup

  1. temperatureThe mixture was refluxed for 1.5 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-19f5e8ca25f6489b975e4ba86a3c07e1
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Linked notes

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