Water → HCID 861848, compound

HRID 2422239Notes

Reaction equation

HRID 2422239 reaction equation
[N:1]1[C:5]2[C:6]3[C:11]([CH2:12][CH2:13][C:4]=2[S:3][C:2]=1[NH2:14])=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].O>N1C=CC=CC=1>[N:1]1[C:5]2[C:6]3[C:11]([CH2:12][CH2:13][C:4]=2[S:3][C:2]=1[NH:14][C:15](=[O:18])[CH2:16][CH3:17])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 7002894,5-Dihydronaphtho[1,2-d][1,3]thiazol-2-amine

Product 1

HCID 861848HCID 861848, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under ice-cooling, to a solution of 4,5-dihydronaphtho[1,2-d][1,3]thiazol-2-amine (1.50 g, 7.4 mmol) in pyridine (20 mL) was added propionyl chloride (1.03 g, 11 mmol), and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1) to give the title compound (1.75 g, yield 91%) as a powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2629ef9223184aec8c5340bab1a54660
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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