1-Bromo-3-methylbutan-2-one → (E)-2-[2-(2-chloro-5-nitrophenyl)ethenyl]-4-(1-methylethyl)thiazole

HRID 1609326Notes

Reaction equation

HRID 1609326 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13](=[S:15])[NH2:14].Br[CH2:17][C:18](=O)[CH:19]([CH3:21])[CH3:20]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13]1[S:15][CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[N:14]=1

Participants

4

Reactant 2

HCID 108990371-Bromo-3-methylbutan-2-oneHCID 20084363HCID 20084363, compound

Product 1

HCID 20084355(E)-2-[2-(2-chloro-5-nitrophenyl)ethenyl]-4-(1-methylethyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of 2.0 g of (E)-3-(2-chloro-5-nitrophenyl)-2-propenethioamide, 3.0 g of 1-bromo-3-methyl-2-butanone and 25 ml of ethyl alcohol was warmed to gentle reflux for 5 hr. The volatiles were then removed in vacuo and the residual materials separated by chromatography over 100 g of alumnia using methylene chloride as the eluant to yield (E)-2-[2-(2-chloro-5-nitrophenyl)ethenyl]-4-(1-methylethyl)thiazole as a yellow solid; m.p. 86°-89° C.

Workup

  1. temperaturewas warmed
  2. temperatureto gentle reflux for 5 hr
  3. customThe volatiles were then removed in vacuo
  4. customthe residual materials separated by chromatography over 100 g of alumnia using methylene chloride as the eluant

Sources & evidence

ORD record
ord-ef79cedaa6f3443ebcddca8c93be326b
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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