Ethanol → HCID 20084364, compound

HRID 327558Notes

Reaction equation

HRID 327558 reaction equation
[CH:1]1([C:9]2[N:10]=[C:11](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)[S:12][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.O.O.[Sn](Cl)Cl>[OH-].[Na+]>[CH:1]1([C:9]2[N:10]=[C:11](/[CH:14]=[CH:15]/[C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[S:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 20084329HCID 20084329, compound

Product 1

HCID 20084364HCID 20084364, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture composed of 2.0 g of (E)-4-cyclooctyl-2-[2-(3-nitrophenyl)ethenyl]thiazole, 50 ml of ethyl alcohol and 4.6 g of tin(II) chloride dihydrate was heated to reflux for 1.2 hr. The cooled reaction mixture was then diluted with 200 ml of 1.5N sodium hydroxide and this mixture was extracted with ethyl ether. The combined extracts were washed with brine, dried (MgSO4) and condensed in vacuo and the residual materials were further purified by silica gel chromatography using ethyl acetate as the eluant to yield 1.8 g of (E)-3-[2-[4-(cyclooctyl)-2-thiazolyl]ethenyl]benzeneamine as an oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.2 hr
  3. customThe cooled reaction mixture
  4. extractionthis mixture was extracted with ethyl ether
  5. washThe combined extracts were washed with brine
  6. customdried
  7. custom(MgSO4) and condensed in vacuo
  8. customthe residual materials were further purified by silica gel chromatography

Sources & evidence

ORD record
ord-4e79b04d221e4a0eb6eb4d626ac39c79
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

Loading…