Potassium Hydroxide → HCID 71467656, compound

HRID 922621Notes

Reaction equation

HRID 922621 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-:8].[K+].[Br:10][CH2:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1>C(#N)C>[Br-:10].[C:18]([CH2:17][O:16][C:15]1[CH:21]=[CH:22][C:12]([CH2:11][N:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([CH2:11][C:12]3[CH:22]=[CH:21][C:15]([O:8][CH2:17][C:18]([OH:20])=[O:19])=[CH:14][CH:13]=3)=[CH:4]2)=[CH:13][CH:14]=1)([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 70106744-(BROMOMETHYL)PHENOXYACETIC ACID

Product 1

HCID 71467656HCID 71467656, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-dichloroimidazole (1.00 g, 7.36 mmol) was dissolved in acetonitrile. Potassium hydroxide (0.828 g, 14.72 mmol) was added to the solution and allowed to reflux for 30 min. 2 equivalents of 2-(4-(bromomethyl)phenoxy)acetic acid (3.61 g, 14.72 mmol) was added to the solution and refluxed for 5 h. Solution was filtered to remove the KBr precipitate and neutralized with 6M HBr. Volatiles were removed in vacuo and the resulting white precipitate was collected and analyzed. 1H NMR (300 MHz, DMSO-d6): δ 4.67, 5.51, 7.12, 7.61, 9.23, 12.17.

Workup

  1. temperatureto reflux for 30 min
  2. temperaturerefluxed for 5 h
  3. filtrationSolution was filtered
  4. customto remove the KBr precipitate
  5. customVolatiles were removed in vacuo
  6. customthe resulting white precipitate was collected

Sources & evidence

ORD record
ord-d08837c2176a41f78d9eaa9d3086e9eb
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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