Hydrochloric Acid → HCID 70043703, compound

HRID 2050569Notes

Reaction equation

HRID 2050569 reaction equation
[C:1](Br)(=[O:5])[CH:2]([CH3:4])[CH3:3].Br.Br.[C:9]1([CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]2[CH:28]=[C:29]([OH:34])[C:30]([OH:33])=[CH:31][CH:32]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[ClH:35]>FC(F)(F)C(O)=O>[C:9]1([CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]2[CH:28]=[C:29]([OH:34])[C:30]([OH:33])=[CH:31][CH:32]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.[ClH:35].[ClH:35].[CH3:3][CH:2]([CH3:4])[C:1]([OH:5])=[O:33].[CH3:3][CH:2]([CH3:4])[C:1]([OH:5])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 520309Isobutyryl bromideHCID 20058556HCID 20058556, compound

Product 1

HCID 70043703HCID 70043703, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Isobutyryl bromide (12 g) was added to a stirred solution of 4-[2-(6-(2-Phenylethylamino)hexylamino) ethyl]-1,2-benzenediol dihydrobromide (4 g) in trifluoracetic acid (100 ml). The solution was then stirred at room temperature for 24 hours. The excess solvent was evaporated and the residue treated with sodium bicarbonate solution. The basic mixture was thoroughly extracted with chloroform. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated to leave a colorless oil which gave a white precipitate when treated with ethereal HCl. The white precipitate was recrystallised to give the title compound from ethanol as colorless prisms (2.8 g), m.p. 232°-234°.

Workup

  1. customThe excess solvent was evaporated
  2. additionthe residue treated with sodium bicarbonate solution
  3. extractionThe basic mixture was thoroughly extracted with chloroform
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a colorless oil which
  9. customgave a white precipitate when
  10. customThe white precipitate was recrystallised

Sources & evidence

ORD record
ord-f6854d385d7a421c9fe45aca0e300546
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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