Sulfuric Acid → HCID 18626530, compound

HRID 1386385Notes

Reaction equation

HRID 1386385 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-8f788a6614e249168de2ceba37fadfc5
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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