Hydrogen Bromide → HCID 19066544, compound

HRID 481446Notes

Reaction equation

HRID 481446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:12][CH2:13]OCC2C=CC=CC=2)=[O:10])=[CH:4][CH:3]=1.Br.O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:9]2=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 19066533HCID 19066533, compound

Product 1

HCID 19066544HCID 19066544, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5.81 g (14.7 mmol) of N-(4-chlorophenyl)-N'-(3-pyridylmethyl)-N'-2-(benzyloxy)ethyl urea in a 100 ml round-bottomed flask were added 65 ml of 48% hydrobromic acid at room temperature. The mixture was heated gradually and then heated for 4 hours at 95° to 100° C. The reaction mixture was cooled to room temperature, 20 ml of water were added, and further 50 ml of ethyl acetate were added to extract. The ethyl acetate layer was extracted with 30 ml of 6N hydrochloric acid, which was combined with previous aqueous layer. While cooling this with ice, pH was made to be 12 or higher with potassium hydroxide and extracted thrice with 100 ml of methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and then solvent was distilled off under reduced pressure to obtain 2.28 g (yield 54%) of 1-(4-chlorophenyl)-3-(3-pyridylmethyl)-2-imidazolidinone as brown crystals.

Workup

  1. temperatureThe mixture was heated gradually
  2. temperatureheated for 4 hours at 95° to 100° C
  3. extractionto extract
  4. extractionThe ethyl acetate layer was extracted with 30 ml of 6N hydrochloric acid, which
  5. temperatureWhile cooling this with ice, pH
  6. extractionhigher with potassium hydroxide and extracted thrice with 100 ml of methylene chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationsolvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b31032e80a8e4decb551397135cc7973
Source dataset
uspto-grants-1998_08
Patent number
US05789425

Reaction notes

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