Cyclopropanecarboxylic acid → N-{6-[(2,6-dichlorobenzyl)oxy]-1,3-benzothiazol-2-yl}cyclopropanecarboxamide

HRID 1929342Notes

Reaction equation

HRID 1929342 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:9]=1[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17]([NH2:19])[S:18][C:14]=2[CH:13]=1>N1C=CC=CC=1>[Cl:7][C:8]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:9]=1[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17]([NH:19][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])[S:18][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 15655Cyclopropanecarboxylic acidHCID 866469386-[(2,6-Dichlorobenzyl)oxy]-1,3-benzothiazol-2-amine

Product 1

HCID 86646937N-{6-[(2,6-dichlorobenzyl)oxy]-1,3-benzothiazol-2-yl}cyclopropanecarboxamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

add 23 mg of cyclopropanecarboxylic acid to a solution of 70 mg of 6-[(2,6-dichlorobenzyl)oxy]-1,3-benzothiazol-2-amine in 1.5 cm3 of anhydrous pyridine. After stirring for one hour at around 20° C., the reaction mixture is concentrated to dryness under reduced pressure (0.2 kPa). The residue is taken up in 25 cm3 of water, then the mixture obtained is extracted three times with 20 cm3 of dichloromethane. The combined organic phases are washed twice with 20 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (92/8 by volume)], we obtain 51 mg of N-{6-[(2,6-dichlorobenzyl)oxy]-1,3-benzothiazol-2-yl}cyclopropanecarboxamide in the form of a cream-coloured powder, which has the following characteristics:

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (0.2 kPa)
  2. customthe mixture obtained
  3. extractionis extracted three times with 20 cm3 of dichloromethane
  4. washThe combined organic phases are washed twice with 20 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (92/8 by volume)], we

Sources & evidence

ORD record
ord-4c0d563e25064802accfe65eec2d6e49
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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