Ethanol → HCID 15729148, compound

HRID 2380589Notes

Reaction equation

HRID 2380589 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:6]=1.[Cl-].[NH4+].C(O)C.O>O1CCCC1.[Fe]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:6]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 189547312-Amino-4-(4-nitrophenylthiomethyl)thiazole

Product 1

HCID 15729148HCID 15729148, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-4-(4-nitrophenylthiomethyl)thiazole (15 g) and ammonium chloride (2 g) in a mixture of tetrahydrofuran (100 ml), ethanol (150 ml) and water was added portionwise added the iron powder (15 g) 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 extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was triturated with chloroform. The precipitates were collected by filtration, washed with ether and dried in vacuo to give 2-amino-4-(4-aminophenylthiomethyl)thiazole (10.50 g, yield: 73.0%).

Workup

  1. additionwas added portionwise
  2. temperatureThe mixture was refluxed for 2 hours
  3. stirringwith stirring
  4. filtrationThe reaction mixture was filtered by suction
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. extractionThe residue was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. customthe residue was triturated with chloroform
  11. filtrationThe precipitates were collected by filtration
  12. washwashed with ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-a6508aac8fa24720b1c0113b97521ad6
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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