Ethanol → HCID 18954742, compound

HRID 1656939Notes

Reaction equation

HRID 1656939 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[Cl-].[NH4+].C(O)C.O>O1CCCC1.[Fe]>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 15729145HCID 15729145, compound

Product 1

HCID 18954742HCID 18954742, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-acetylamino-4-(4-nitrophenylthiomethyl)thiazole (11 g) and ammonium chloride (2 g) in a mixture of tetrahydrofuran (200 ml), ethanol (200 ml) and water (100 ml) was added portionwise the iron powder (17 g) at 80° C. with stirring. The mixture was refluxed for 3 hours with stirring. The reaction mixture was filtered by suction and the filtrate was concentrated under reduced pressure and then the residue was triturated with water. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-acetylamino-4-(4-aminophenylthiomethyl)thiazole (9.3 g, yield: 93.6%).

Workup

  1. temperatureThe mixture was refluxed for 3 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-2b7f96dd6abc47b6b1f8b1c1eb0b90ab
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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