Sodium Hydroxide → 4-(1,3-Thiazol-2-yl)aniline

HRID 450104Notes

Reaction equation

HRID 450104 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>C(O)(=O)C.O.[Fe]>[S:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 13546655HCID 13546655, compound

Product 1

HCID 34747844-(1,3-Thiazol-2-yl)anilineYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Iron powder (0.5 g, 8.92 mmol) was added portion wise to a solution of 2-(4-nitrophenyl)-thiazole (200 mg, 0.97 mmol) in acetic acid (5 ml) and stirred at room temperature for 2 hr. The reaction mixture was diluted with water, basified with dilute sodium hydroxide, filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation of the solvent yielded 4-thiazol-2-yl-phenylamine (150 mg, 88%) as solid.

Workup

  1. filtrationfiltered
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4a09f232655d4742bea652a536135fc8
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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