Hydrochloric Acid → HCID 22648854, compound

HRID 393284Notes

Reaction equation

HRID 393284 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)=O.CC[N:15]([CH2:18]C)CC.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C([NH2:43])=O>CN(C=O)C.CCOC(C)=O>[CH3:12][C:7]1[CH:6]=[C:5]([C:3]2[N:43]=[CH:18][N:15]([C:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:2]=2)[CH:10]=[CH:9][C:8]=1[OH:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

Product 1

HCID 22648854HCID 22648854, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-bromo-1-(4-hydroxy-3-methylphenyl)ethanone (400 mg, 1.75 mmol) in formamide (10 mL) was stirred at 190° C. for 5 h. The excess formamide was distilled under reduced pressure. The residue was taken in EtOAc (50 mL) and the resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. A solution of the residue, Et3N (0.88 g, 8.73 mmol) and triphenylmethyl chloride (584 mg, 2.10 mmol) in DMF (10 mL) was stirred at 60° C. for 3 h. The reaction mixture was cooled to 25° C., acidified with aqueous 1.0 N HCl solution and diluted with EtOAc (200 mL). The resulting mixture was successively washed with water (3×50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to yield the title compound (514 mg, 71% yield).

Workup

  1. distillationThe excess formamide was distilled under reduced pressure
  2. washthe resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL)
  3. dry with materialthen was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting mixture was successively washed with water (3×50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-ffd4d76f870e4305ac6cc04a520d9816
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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