1-Bromooctane → HCID 3715235, compound

HRID 1034339Notes

Reaction equation

HRID 1034339 reaction equation
[CH3:1][C:2]1[NH:3][NH:4][C:5](=[O:7])[CH:6]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>>[CH3:1][C:2]1[CH2:6][C:5](=[O:7])[N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:3]=1

Participants

3

Reactant 2

HCID 81401-BromooctaneHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 3715235HCID 3715235, compoundYield 42%

Conditions

Temperature
135 °C

Procedure

A mixture of 19.63 g 3-methyl-3-pyrazolin-5-one and 42.30 g 1-bromooctane was stirred and heated at 135° C. for 50 hour. After cooling, the reaction mixture was triturated with 200 ml water, treated with 17.00 g sodium bicarbonate in small portions, and heated to 100° C. for 1 hour. After cooling, the mixture was extracted with chloroform (3×100 ml portions). The combined extracts were dried over anhydrous calcium chloride and the solvent evaporated to give an oily residue crystallized from hexane (at -5° C.) to give 2,4-dihydro-5-methyl-2-octyl-3H-pyrazol-3-one (17.50 g, 42% yield) as white plates, m.p. 59° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was triturated with 200 ml water
  3. additiontreated with 17.00 g sodium bicarbonate in small portions
  4. temperatureheated to 100° C. for 1 hour
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with chloroform (3×100 ml portions)
  7. dry with materialThe combined extracts were dried over anhydrous calcium chloride
  8. customthe solvent evaporated
  9. customto give an oily residue
  10. customcrystallized from hexane (at -5° C.)

Sources & evidence

ORD record
ord-0013009f20db437191d4f1e9cbb21a68
Source dataset
uspto-grants-1994_05
Patent number
US05314998

Reaction notes

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