Sodium Acetate → 4-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine

HRID 556038Notes

Reaction equation

HRID 556038 reaction equation
Br[CH:2]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:23][C:24]([NH2:26])=[S:25].C([O-])(=O)C.[Na+]>C(O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:23]=[C:24]([NH2:26])[S:25][C:2]=2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 866366252-Bromo-1-(4-methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one

Product 1

HCID 579916084-(4-Methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamineYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 ml eggplant-shaped flask were added 0.45 g (1.24 mmol) 2-bromo-1-(4-methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one prepared in the step 4 and 15 ml anhydrous ethanol, added 94 mg (1.24 mmol) thiourea and 101 mg (1.24 mmol) anhydrous sodium acetate under stirring. The resulting mixture was refluxed for 3 hours, distilled under a reduced pressure to remove the solvent, added 20 ml ethyl acetate and 20 ml 5% NaHCO3 aqueous solution, the organic layer was separated, washed with saturated brine until neutrality, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product, which was recrystallized with ethyl acetate to obtain a 0.34 product in a yield of 79.1%, mp: 209-210 └(Dec.). 1H-NMR (DMSO-d6, 400 MHz) δ: 3.34 (3H, s, OCH3), 4.20 (2H, s, CH2), 6.93 (2H, s, NH2), 6.95 (2H, d, J=8.72 Hz, ArH), 7.43˜7.46 (4H, m, ArH), 8.19 (2H, d, J=8.72 Hz, ArH); EI-MS m/e (%): 341.2 (M+, 100), 219.1 (14); HREI-MS Calcd. for C17H15N3O3S: 341.0834. found: 341.0834. Anal. Calcd. for C17H15N3O3S: C, 59.81; H, 4.43; N, 12.31. found: C, 59.76; H, 4.36; N, 12.05.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. distillationdistilled under a reduced pressure
  3. customto remove the solvent
  4. additionadded 20 ml ethyl acetate and 20 ml 5% NaHCO3 aqueous solution
  5. customthe organic layer was separated
  6. washwashed with saturated brine until neutrality
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9c1c314826f6476e90ec20f970338597
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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