Sodium Acetate → 2-Amino-4-(p-nitrophenyl)thiazole

HRID 737156Notes

Reaction equation

HRID 737156 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([O-])(=O)[CH3:6].[Na+].BrCC(O)=O.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:17])=[O:16]>C(O)C>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([C:5]2[N:1]=[C:2]([NH2:4])[S:3][CH:6]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 86616428Nitrobenzene bromoacetate

Product 1

HCID 164202-Amino-4-(p-nitrophenyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (13.2 mmol) of thiourea, sodium acetate (2.2 g 26.4 mmol), and 25 mL of dry ethanol were combined in a 25 mL round bottom flask. To this suspension was added nitrobenzene bromoacetate (4.2 g, 1.72 mmol). Reaction mixture was heated under reflux overnight. This suspension was cooled to room temperature. The solid was collected by suction filtration and washed using water. The resulting solid was dried to yield 4-(4-nitro-phenyl)-thiazol-2-ylamine. MS: 222.1 (M+H+).

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux overnight
  4. filtrationThe solid was collected by suction filtration
  5. washwashed
  6. customThe resulting solid was dried

Sources & evidence

ORD record
ord-8a16edf569124b38bd4b712354421325
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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