HCID 15136077, compound → HCID 20084329, compound

HRID 327557Notes

Reaction equation

HRID 327557 reaction equation
[CH:1]1([C:9]([CH2:11]Br)=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:13]([C:16]1[CH:17]=[C:18](/[CH:22]=[CH:23]/[C:24](=[S:26])[NH2:25])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>C(O)C>[CH:1]1([C:9]2[N:25]=[C:24](/[CH:23]=[CH:22]/[C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=3)[S:26][CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15136077HCID 15136077, compoundHCID 20084345HCID 20084345, compound

Product 1

HCID 20084329HCID 20084329, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of 6.2 g of bromomethyl cyclooctyl ketone, 5.6 g of (E)-3-(3-nitrophenyl)-2-propenethioamide and 75 ml of ethyl alcohol was heated to reflux for 1 hr afterwhich it was diluted with 200 ml of ice water and extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4) and condensed in vacuo to give an oil which was further purified by chromatography over florisil using methylene chloride as the eluant to yield 4.5 g of (E)-4-cyclooctyl-2-[2-(3-nitrophenyl)ethenyl]thiazole; m.p. 64°-65° C. after crystallization from ethyl alcohol.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr afterwhich it
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. customdried
  6. custom(MgSO4) and condensed in vacuo
  7. customto give an oil which
  8. customwas further purified by chromatography over florisil

Sources & evidence

ORD record
ord-eabd475fbcef463cbed7f87c5dc5705d
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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