Ethyl bromoacetate → HCID 13588740, compound

HRID 1666706Notes

Reaction equation

HRID 1666706 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][CH:13]=O.BrC[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][CH2:13][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 4090563Formamide, N-2-benzothiazolyl- (6CI,7CI,8CI,9CI)

Product 1

HCID 13588740HCID 13588740, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the suspension of 0.2 g (5 mmol) 60% sodium hydride in 5 ml dimethylformamide in small portions 0.89 g (5 mmol) 1,3-benzothiazol-2-ylformamide, then after 30 minutes of stirring, dropwise the solution of 0.92 g (5.5 mmol) ethyl bromoacetate in 2 ml dimethylformamide are added and the mixture is stirred at room temperature for 4 hours. The reaction mixture is poured onto ice-water mixture, the precipitated crystals are filtered off. 0.85 g title compound is obtained. LC/MS[MH+]=237 (C11H12N2O2S 236.294). The mixture of N2-1,3-benzothiazol-2-yl-N1-{3-[(3,4-dichlorobenzyl)(methyl)amino]propyl}glicinamide 0.68 g (2.88 mmol) ethyl N-1,3-benzothiazol-2-ylglicinate and 0.81 g (2.88 mmol) N-(3,4-dichlorobenzyl)-N-(methyl)propane-1,3-diamine is heated at 100° C. for 2 hours. The crude melt is purified by column chromatography using chloroform-methanol 19:1 mixture as eluent. 500 mg title compound is obtained as crystals.

Workup

  1. stirringthe mixture is stirred at room temperature for 4 hours
  2. additionThe reaction mixture is poured onto ice-water mixture
  3. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-058034e8e84347de8c40ac6c35161141
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

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