Sulfuric Acid → HCID 18626530, compound

HRID 1859789Notes

Reaction equation

HRID 1859789 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:20]([C:22]1[S:23][CH:24]=[CH:25][N:26]=1)=[O:21].OS(O)(=O)=O>CC(O)=O.O>[OH:21][CH:20]([C:22]1[S:23][CH:24]=[CH:25][N:26]=1)[CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:10]=2)[C:15]1=[O:19]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 18626530HCID 18626530, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

6-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.200 g, 0.78 mmol) was reacted with 2-formylthiazole (0.107 g, 0.94 mmol) in a mixture of HOAc (1 mL) and concentrated H2SO4 (0.100 mL) at room temperature overnight. The resulting biphasic reaction mixture was diluted with water and then extracted with EtOAc. The aqueous portion was made to pH 10 with 50% NaOH and extracted with EtOAc (3×50 mL). The pooled organic extracts were washed well with water, dried, filtered, and concentrated to afford 0.215 g (74%) of the title compound as a golden oil: APCI-MS m/e 370.2 M++1).

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe pooled organic extracts were washed well with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f17643784414ff9926ec70098bf6260
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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