Ethyl Acetate → HCID 59806022, compound

HRID 1441700Notes

Reaction equation

HRID 1441700 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:14][CH2:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH2:27][CH2:28][CH2:29][CH3:30].C(OCC)(=O)C>CN(C)C=O>[CH2:27]([N:14]([CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)[C:11]1[S:12][CH:13]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 59164604HCID 59164604, compound

Product 1

HCID 59806022HCID 59806022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g 4-{[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-methyl}-benzonitrile was dissolved in 150 ml dimethylformamide. 150 mg sodium hydride (24% in mineral oil) were added and the reaction mixture stirred at room temperature for thirty minutes. Then 0.43 ml 1-Iodobutane were added and the reaction mixture stirred at room temperature for two hours. Then 100 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml water and then dried over MgSO4. The solvents were removed in vacuo to obtain 1.2 g 4-({Butyl-[4-(4-methoxy-phenyl)-thiazol-2-yl]-amino}-methyl)-benzonitrile.

Workup

  1. stirringthe reaction mixture stirred at room temperature for two hours
  2. washthe mixture was washed three times with portions of 50 ml water
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-12c3fc2653804f1d82662a198b21a355
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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