Laurolactam → HCID 20068281, compound

HRID 982572Notes

Reaction equation

HRID 982572 reaction equation
[C:1]1(=[O:14])[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)Cl.[Br:21]Br>C(Cl)(Cl)Cl.II>[Br:21][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:1](=[O:14])[CH2:2]1

Participants

6

Reactant 3

HCID 13690LaurolactamHCID 24408BromineHCID 24819Phosphorus pentachloride

Product 1

HCID 20068281HCID 20068281, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 6212ChloroformSolvent

Procedure

19.7 g of laurolactam in 100 ml of chloroform were cooled to 0° C. 20.8 g of phosphorus pentachloride were added portionwise over a period of 40 minutes while keeping the temperature below 5° C. There was then added 0.2 g of iodine, followed by 16.0 g (0.2 mol) of bromine over a period of 20 minutes. The mixture was heated under reflux for 4 hours, cooled, evaporated and poured on to ice. The product was taken up in chloroform, washed with sodium hydrogen sulfate solution, dried over anhydrous magnesium sulfate and evaporated. Crystallization from chloroform/ n-hexane yielded 12.65 g (46%) of 3-bromolaurolactam of melting point 155°-157° C.

Workup

  1. customthe temperature below 5° C
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperaturecooled
  5. customevaporated
  6. additionpoured on to ice
  7. washwashed with sodium hydrogen sulfate solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customCrystallization from chloroform/ n-hexane

Sources & evidence

ORD record
ord-1fcf372783be4fca823884473ac4aa1d
Source dataset
uspto-grants-1991_02
Patent number
US04996358

Reaction notes

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