N,N-Diethylaniline → 2-Chlorocycloheptimidazole

HRID 1194293Notes

Reaction equation

HRID 1194293 reaction equation
O[C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=[C:5]2[N:6]=1.P(Cl)(Cl)([Cl:14])=O.C(N(CC)C1C=CC=CC=1)C>>[Cl:14][C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=[C:5]2[N:6]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychloride2×HCID 178517150HCID 178517150, compound

Product 1

HCID 200643702-Chlorocycloheptimidazole

Conditions

Temperature
70 °C

Procedure

With reference to the method disclosed in Chemical and Pharmaceutical Bulletin, vol. 16, No. 7, pages 1300 to 1307 (1968), 10 g of 2-hydroxycycloheptimidazole, 150 g of phosphorus oxychloride and 12 g of N,N-diethylaniline were stirred with heating to the inner temperature of 70° C. for 6 hours and 30 minutes. After the reaction, phosphorus oxychloride was distilled away under reduced pressure and 500 ml of ice water was added to the residue. Then, a sodium bicarbonate solution was added thereto to neutral pH, and extracted with chloroform (250 ml×2). The chloroform layer was dried over anhydrous sodium sulfate, solvent was distilled away, and the residue was purified by silica gel column chromatography using ethyl acetate as a developing solvent.

Workup

  1. distillationwas distilled away under reduced pressure and 500 ml of ice water
  2. additionwas added to the residue
  3. additionThen, a sodium bicarbonate solution was added
  4. extractionto neutral pH, and extracted with chloroform (250 ml×2)
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate, solvent
  6. distillationwas distilled away
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c9fd69cf4b34addb0aa409c569b86a9
Source dataset
uspto-grants-1989_03
Patent number
US04814265

Reaction notes

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