Ethanol → N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide

HRID 1484706Notes

Reaction equation

HRID 1484706 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]([NH2:20])=[S:19].CCO>C1(C)C=CC=CC=1>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=2[CH3:16])[N:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 118006191N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamide

Product 1

HCID 58442517N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamideYield 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of compound N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamide (3.4 g, 14.2 mmol), thiourea (1.79 g, 23.6 mmol) and KI (150 mg) in toluene (50 mL) and 95% EtOH (50 mL) was refluxed overnight. After the solvent was distilled off, the residue was dissolved in EtOAc (600 mL) and washed with saturated Na2CO3 solution and brine successively, and dried over Na2SO4. After removal of solvent, the residue was subjected to column chromatography (silica gel, EtOAc:NH4OH=100:0.5) to furnish N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide (3.2 g, 86.1% yield).

Workup

  1. distillationAfter the solvent was distilled off
  2. dissolutionthe residue was dissolved in EtOAc (600 mL)
  3. washwashed with saturated Na2CO3 solution and brine successively
  4. dry with materialdried over Na2SO4
  5. customAfter removal of solvent

Sources & evidence

ORD record
ord-fcb32aa84d0942b585bb790b1a1362c7
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

Loading…