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

HRID 2190361Notes

Reaction equation

HRID 2190361 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.[OH-].[Li+].[OH-].[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.O>[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

8

Reactant 4

HCID 14798Sodium HydroxideHCID 334622-Amino-6-benzothiazololHCID 77637Cyclopropanecarbonyl chlorideHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamideYield 76%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-1,3-benzothiazol-6-ol (3.43 g, 20.6 mmol) in pyridine (50 mL) were added cyclopropanecarbonyl chloride (4 mL, 44.1 mmol) and N,N-dimethylpyridine-4-amine (220 mg, 1.80 mmol), and the mixture was stirred at room temperature for 1.5 hr. To the reaction mixture was added lithium hydroxide monohydrate (2.06 g, 49.1 mmol) in water (50 mL) and the mixture was stirred at the same temperature for 1 hr. 5N Aqueous sodium hydroxide solution (50 mL) was added, and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dilute hydrochloric acid (300 mL, pH 2.0), and extracted with ethyl acetate (250 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (150 mL). The earlier aqueous layer was extracted with ethyl acetate (150 mL), and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (100 mL). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.67 g, 76%) as a pale-gray solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. stirringthe mixture was stirred at room temperature for 2 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in dilute hydrochloric acid (300 mL, pH 2.0)
  5. extractionextracted with ethyl acetate (250 mL)
  6. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (150 mL)
  7. extractionThe earlier aqueous layer was extracted with ethyl acetate (150 mL)
  8. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (100 mL)
  9. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  10. filtrationthe insoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ff31071ca5d48fe9fdf11fd8fcab32f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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