Ethanol → 2-Formylamino-4-(4-aminophenylthiomethyl)thiazole

HRID 1656971Notes

Reaction equation

HRID 1656971 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[N:8]=1)=[O:2].[Cl-].[NH4+].C(O)C.O>O1CCCC1.[Fe]>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 15729170HCID 15729170, compound

Product 1

HCID 157291712-Formylamino-4-(4-aminophenylthiomethyl)thiazoleYield 81%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-formylamino-4-(4-nitrophenylthiomethyl)thiazole (2.2 g) and ammonium chloride (0.5 g) in a mixture of tetrahydrofuran (30 ml), ethanol (50 ml) and water (10 ml) was added portionwise 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 residue was triturated with water. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-formylamino-4-(4-aminophenylthiomethyl)thiazole (1.6 g, yield: 81%). mp: 180°-182° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. stirringwith stirring
  3. filtrationThe reaction mixture was filtered by suction
  4. customthe residue was triturated with water
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8edd794016874f1ba35246534b43a515
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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