Sodium Chloride → HCID 10678882, compound

HRID 1595159Notes

Reaction equation

HRID 1595159 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:8])=[CH:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>O>[CH3:1][N:2]1[C:3]2[C:12](=[O:14])[CH2:11][CH2:10][NH:9][C:7](=[O:8])[C:4]=2[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 10821710HCID 10821710, compound

Product 1

HCID 10678882HCID 10678882, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 4 (348 mg, 1.5 mmole) and polyphosphoric acid (80%, 17.5 g) was stirred at 100° C. for 1 hour. Water (150 ml) was added to the reaction mixture, followed by the addition of potassium carbonate to adjust the pH to 5. The resulting mixture was saturated with sodium chloride and then extracted with THF (3 times). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was fractionated and purified by chromatography on a silica gel column (eluent: 3%-methanol/chloroform), whereby Compound 5 (161 mg) was obtained (yield: 50%).

Workup

  1. extractionextracted with THF (3 times)
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography on a silica gel column (eluent: 3%-methanol/chloroform)

Sources & evidence

ORD record
ord-39fbcde5c9bb44df9fadaed5d2be4421
Source dataset
uspto-grants-2001_09
Patent number
US06288056B1

Reaction notes

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