Ethyl Acetate → HCID 59164604, compound

HRID 1441699Notes

Reaction equation

HRID 1441699 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:14])[S:12][CH:13]=2)=[CH:5][CH:4]=1.Br[CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([NH:14][CH2:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[S:12][CH:13]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 869964-(Bromomethyl)benzonitrileHCID 1596442-Amino-4-(4-methoxyphenyl)thiazole

Product 1

HCID 59164604HCID 59164604, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g 4-(4-Methoxyphenyl)-1,3-thiazol-2-amine, 4.29 g 4-bromomethyl-benzonitrile and 6.0 ml N,N-Diisopropylethylamine were suspended in 20 ml dimethylformamide. The reaction mixture was stirred under microwave irradiation at 100° C. for thirty minutes. The cooled reaction mixture was diluted by the addition of 100 ml ethyl acetate and washed 50 ml saturated NaHCO3 solution and the dried over MgSO4. The solvent was removed in vacuo and the resulting residue was purified by chromatography on silica gel with the eluent petroleum ether: ethyl acetate=3:2 to obtain 2.41 g 4-{[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-methyl}-benzonitrile.

Workup

  1. customThe cooled reaction mixture
  2. washwashed 50 ml saturated NaHCO3 solution
  3. dry with materialthe dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe resulting residue was purified by chromatography on silica gel with the eluent petroleum ether

Sources & evidence

ORD record
ord-207c326459d04a21909785d9f24d69b8
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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