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

HRID 1874377Notes

Reaction equation

HRID 1874377 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.C(N(CC)CC)C.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>O1CCCC1.O>[OH:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])[S:3][C:4]=2[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 334622-Amino-6-benzothiazololHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-1,3-benzothiazol-6-ol (9.03 g, 54.3 mmol) and triethylamine (8.27 mL, 59.7 mmol) in tetrahydrofuran (100 mL) was added with stirring under ice-cooling a solution of cyclopropanecarbonyl chloride (5.19 mL, 57.0 mmol) in tetrahydrofuran (25 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with hexane-ethyl acetate to give the title compound (12.3 g, 97%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationthe residue was collected by filtration
  8. washwashed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-4220a1cd57df4748a9613693d298f0d3
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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