Diethyl Ether → HCID 58016053, compound

HRID 1400168Notes

Reaction equation

HRID 1400168 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[N:12]=[CH:13][S:14][C:15]=2C(O)=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N-:19]=[N+]=[N-].[Na+].C([O:25][CH2:26]C)C>C1C=CC=CC=1.O>[N:12]1[C:11]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:26](=[O:25])[NH:19][C:15]=2[S:14][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 134413294-Phenylthiazole-5-carboxylic acid

Product 1

HCID 58016053HCID 58016053, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (1 ml) was added to a suspension of 4-phenyl-1,3-thiazole-5-carboxylic acid (300 mg, 1.46 mmol) in 10 ml of dry benzene and the mixture was refluxed for 2 hours. The solvent and the excess of thionyl chloride were removed under reduced pressure; the residue was taken up using 10 ml of dry THF and cooled to 0° C. Sodium azide (1.5 mmol) dissolved in the minimal amount of water was quickly added and the resulting solution was stirred for 1 hour at room temperature. After pouring into 100 ml of cracked ice/H2O and extraction with diethyl ether (4×100 ml), the collected organic layers were dried over Na2SO4. The filtrate was gently evaporated under reduced pressure, the residue was dissolved in 10 ml of o-dichlorobenzene, and the resulting mixture was refluxed for 5-10 hours. The mixture was then cooled, and directly submitted to flash chromatography, elution with dichloromethane/methanol (99/1) afforded to the title compound. Yield: 20%.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe solvent and the excess of thionyl chloride were removed under reduced pressure
  3. additionwas quickly added
  4. dry with materialthe collected organic layers were dried over Na2SO4
  5. customThe filtrate was gently evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in 10 ml of o-dichlorobenzene
  7. temperaturethe resulting mixture was refluxed for 5-10 hours
  8. temperatureThe mixture was then cooled
  9. washdirectly submitted to flash chromatography, elution with dichloromethane/methanol (99/1)

Sources & evidence

ORD record
ord-ef489d1ffafc46f5a34b9ca29019b7e1
Source dataset
uspto-grants-2014_12
Patent number
US08906935B2

Reaction notes

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