Water → Thiazosulfone

HRID 2380584Notes

Reaction equation

HRID 2380584 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 no give 2-amino-5-(4-aminophenylsulfonyl)thiazole (3.10 g, yield: 86.6%).

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

Sources & evidence

ORD record
ord-efbcddf1e8d944149e6d7fde72587e72
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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