Water → N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide

HRID 2095768Notes

Reaction equation

HRID 2095768 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:12]1([C:15](Cl)=[O:16])[CH2:14][CH2:13]1.O>CN(C)C(=O)C>[OH:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:15]([CH:12]3[CH2:14][CH2:13]3)=[O:16])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 334622-Amino-6-benzothiazololHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-amino-1,3-benzothiazol-6-ol (4.99 g, 30.0 mmol) in N,N-dimethylacetamide (20 mL) was added cyclopropanecarbonyl chloride (4.08 mL, 45.0 mmol) at 0° C., and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed 3 times with water, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/diisopropyl ether and collected by filtration to give the title compound (3.22 g, 13.7 mmol) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed 3 times with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with ethyl acetate/diisopropyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7b0c455c3b5a4b84af6a391be3e3fce9
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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