Potassium Carbonate → 2-(1,3-Benzothiazol-2-yloxy)-N-{3-[(3,4-dichlorobenzyl)(methyl)amino]propyl}-acetamide

HRID 1666701Notes

Reaction equation

HRID 1666701 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)[CH3:26])=[O:20]>CN(C)C=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][CH2:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)[CH3:26])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674425202-bromo-N-{3-[(3,4-dichlorobenzyl)(methyl)amino]propyl}acetamideHCID 178517143HCID 178517143, compound

Product 1

HCID 160691902-(1,3-Benzothiazol-2-yloxy)-N-{3-[(3,4-dichlorobenzyl)(methyl)amino]propyl}-acetamideYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.0756 g (0.5 mmol) 1,3-benzothiazol-2-ol is dissolved in 5 ml dimethylformamide, 0.15 g (1.1 mmol) dry potassium carbonate is added and under stirring at room temperature 0.18 g (0.5 mmol) 2-bromo-N-{3-[(3,4-dichlorobenzyl)(methyl)amino]propyl}acetamide in 2 ml dimethylformamide is added dropwise. Stirring is continued for 24 hours. The reaction mixture is poured onto ice-water mixture, the precipitated crystals are filtered off, washed with water to obtain 0.13 g title compound. Mp: 113-115° C.

Workup

  1. additionis added dropwise
  2. additionThe reaction mixture is poured onto ice-water mixture
  3. filtrationthe precipitated crystals are filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-0cc62e5e8da04eb39edd9f5c9e08c7cd
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

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