HCID 15136077, compound → HCID 20084322, compound

HRID 1609316Notes

Reaction equation

HRID 1609316 reaction equation
[CH:1]1([C:8]([CH2:10]Br)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:12]([C:15]1[CH:16]=[C:17](/[CH:21]=[CH:22]/[C:23](=[S:25])[NH2:24])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>C(O)C>[CH:1]1([C:8]2[N:24]=[C:23](/[CH:22]=[CH:21]/[C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=3)[S:25][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15136077HCID 15136077, compoundHCID 218423502-Bromo-1-cycloheptylethan-1-one

Product 1

HCID 20084322HCID 20084322, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of 6.57 g of bromomethyl cycloheptyl ketone, 6.24 g of (E)-3-(3-nitrophenyl)-2-propenethioamide and 100 ml of ethyl alcohol was heated to reflux for 16 hr afterwhich it was diluted with 200 ml of ice water and extracted with methylene chloride. The combined extracts were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and condensed in vacuo to yield 6.17 g of (E)-4-cycloheptyl-2-[2-(3-nitrophenyl)ethenyl]thiazole; m.p. 60° C. after crystallization from ethyl ether/hexane.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr afterwhich it
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with saturated sodium bicarbonate, brine
  5. customdried
  6. custom(MgSO4) and condensed in vacuo

Sources & evidence

ORD record
ord-440ee59629f549eba729bc9fb4e8f08a
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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