Phosphorus pentachloride → HCID 10611487, compound

HRID 378878Notes

Reaction equation

HRID 378878 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.S[C:8]1[O:9][C:10]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 531671-MethylpiperazineHCID 178526474HCID 178526474, compound

Product 1

HCID 10611487HCID 10611487, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus pentachloride (764 mg) was dissolved in anhydrous toluene (9 ml), the resulting solution was mixed with 2-mercapto-6-nitrobenzoxazole (600 mg) which has been obtained in the same manner as described in Reference Example 1, and the mixture was then stirred with heating at 100° C. for 3 hours. With cooling in an ice bath, to this was added dropwise N-methylpiperazine (3.4 ml). After 20 minutes of stirring, the thus obtained mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order. After drying with magnesium sulfate, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1) to obtain 2-(4-methyl-1-piperazinyl)-6-nitrobenzoxazole (668.9 mg) in the form of yellow crystalline powder.

Workup

  1. customhas been obtained in the same manner
  2. temperatureWith cooling in an ice bath
  3. stirringAfter 20 minutes of stirring
  4. extractionthe thus obtained mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  6. dry with materialAfter drying with magnesium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-d98601c09bd34b09928a8888e5579569
Source dataset
uspto-grants-2001_10
Patent number
US06297246B1

Reaction notes

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