N-(5-Furan-3-yl-4-phenyl-thiazol-2-yl)-formamide → 5-Furan-3-yl-4-phenyl-thiazol-2-ylamine

HRID 604480Notes

Reaction equation

HRID 604480 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:10][C:9]([NH:11]C=O)=[N:8][C:7]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:2]1>CO.C1COCC1.Cl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:10][C:9]([NH2:11])=[N:8][C:7]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:2]1

Participants

5

Reactant 1

HCID 57709597N-(5-Furan-3-yl-4-phenyl-thiazol-2-yl)-formamide

Product 1

HCID 577096105-Furan-3-yl-4-phenyl-thiazol-2-ylamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Furan-3-yl-4-phenyl-thiazol-2-yl)-formamide (5.7 g, 21 mmol) was dissolved in a mixture of methanol (210 mL) and THF (90 mL), and conc. squeous hydrochloric acid (8.7 mL) was added dropwise at room temperature. The reaction mixture was stirred over night and the solvent was removed by evaporation. The residue was extracted with ethyl acetate, and washed with NaHCO3 (aq.; sat.) and water and dried over sodium sulfate. The solvent was removed and the crude product was purified on neutral Al2O3 using 30-35% ethyl acetate in hexane as eluent. Yield: 2.5 g, 49%.

Workup

  1. additionwas added dropwise at room temperature
  2. customthe solvent was removed by evaporation
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with NaHCO3 (aq.; sat.) and water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed
  7. customthe crude product was purified on neutral Al2O3 using 30-35% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-6890e186cbf1464eaad905c868b0c5c7
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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