Cyclopropanecarbonyl chloride → HCID 67311146, compound

HRID 2190485Notes

Reaction equation

HRID 2190485 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:22]1([C:25]([NH:1][C:2]2[O:3][C:4]3[CH:10]=[C:9]([O:11][C:12]4[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=4)[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:26])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride3×HCID 67311166HCID 67311166, compound

Product 1

HCID 67311146HCID 67311146, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution (100 mL) of methyl 3-[(2-amino-1,3-benzooxazol-6-yl)oxy]benzoate (6.84 g, 24.1 mmol) in pyridine were added N,N-dimethylpyridine-4-amine (129 mg, 1.05 mmol) and cyclopropanecarbonyl chloride (2.5 mL, 27.5 mmol), and the mixture was stirred at room temperature for 1.5 hr. To the reaction mixture was added cyclopropanecarbonyl chloride (2.5 mL, 27.5 mmol), and the mixture was further stirred at room temperature for 1.5 hr. Cyclopropanecarbonyl chloride (1.5 mL, 16.5 mmol) was further added to the reaction mixture, and the mixture was continuously stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate (200 mL). This suspension was washed with 0.1N hydrochloric acid (150 mL) and saturated aqueous sodium hydrogencarbonate solution (150 mL), successively. The diluted hydrochloric acid layer was extracted with ethyl acetate (100 mL×2), and the combined organic layers were washed with saturated aqueous sodium hydrogencarbonate solution (150 mL) and saturated brine (150 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give a brown amorphous substance (8.2 g).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1.5 hr
  2. stirringthe mixture was continuously stirred at room temperature for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washThis suspension was washed with 0.1N hydrochloric acid (150 mL) and saturated aqueous sodium hydrogencarbonate solution (150 mL)
  5. extractionThe diluted hydrochloric acid layer was extracted with ethyl acetate (100 mL×2)
  6. washthe combined organic layers were washed with saturated aqueous sodium hydrogencarbonate solution (150 mL) and saturated brine (150 mL)
  7. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated
  10. customto give a brown amorphous substance (8.2 g)

Sources & evidence

ORD record
ord-883d3284b336484399959a126ffba973
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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