Sodium Carbonate → HCID 66933727, compound

HRID 1363334Notes

Reaction equation

HRID 1363334 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19]C)[CH:13]=[C:12]([O:21]C)[C:11]=2[C@@H:23]1[CH2:27][CH2:26][N:25]([CH3:28])[C@H:24]1[CH2:29][OH:30].Cl.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([OH:19])[CH:13]=[C:12]([OH:21])[C:11]=2[C@@H:23]1[CH2:27][CH2:26][N:25]([CH3:28])[C@H:24]1[CH2:29][OH:30]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 66933949HCID 66933949, compound

Product 1

HCID 66933727HCID 66933727, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of compound of example 16 (0.36 g, 0.76 mmol) and dry pyridine hydrochloride (3.6 g, 31.6 mmol) was heated at 180° C. for 1.5 h. The reaction mixture was cooled to room temperature, treated with water (50 mL) and basified using an aqueous saturated Na2CO3 solution. It was extracted using CHCl3 (3×100 mL). The organic extract was washed with water, dried (anhydrous Na2SO4) and concentrated. Traces of pyridine were removed using high vacuum. Purification was carried out using a silica gel column and a mixture of 5% methanol+1% liquor ammonia in CHCl3 as eluant to obtain title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionIt was extracted
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customTraces of pyridine were removed
  8. customPurification
  9. additiona mixture of 5% methanol+1% liquor ammonia in CHCl3 as eluant

Sources & evidence

ORD record
ord-22adff9fba904c89b6f90526384c5f44
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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