1-Bromododecane → HCID 54172828, compound

HRID 2106627

Reaction equation

HRID 2106627 reaction equation
[OH-:1].[K+].[NH:3]1[C:10](=[S:11])[NH:9][C:7](=[S:8])[NH:6][C:4]1=[S:5].Br[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:14]([OH:16])=[O:15].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(O)C>[CH2:27]([S:5][C:4]1[N:6]=[C:7]([S:8][CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:14]([OH:16])=[O:15])[N:9]=[C:10]([S:11][CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:14]([OH:15])=[O:1])[N:3]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 89191-BromododecaneHCID 14797Potassium Hydroxide2×HCID 669802-Bromododecanoic acidHCID 1268121Trithiocyanuric acid

Product 1

HCID 54172828HCID 54172828, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred solution of KOH (5.6 g; 0.1 mole) in ethanol (100 ml) is cooled to 5-10° C. and treated with trithiocyanuric acid (4.42 g; 0.025 mole). After stirring for 30 minutes, the reaction mixture is treated with 2-bromododecanoic acid (13.9 g; 0.05 mole) in small portions over 10-15 minutes. The resulting white suspension is stirred for a further 30 minutes at 10° C. and is then allowed to warm to ambient temperature. Upon reaching ambient temperature, the reaction mixture is heated to reflux and maintained at this temperature for 3 hours. The reaction mixture is then cooled to 5° C. and treated with a solution of KOH (1.4 g; 0.025 mole) in ethanol (50 ml) followed by dodecyl bromide (6.2 g; 0.025 mole). The reaction mixture is allowed to warm to ambient temperature and is then heated to reflux and maintained at this temperature for 2 hours. The reaction mixture is cooled to ambient temperature and the solvent removed under reduced pressure. The residue is suspended in water (100 ml and acidified with concentrated HCl to pH 3. The acidified aqueous suspension is then extracted with either (200 ml) and the ether extract is washed with water (3×50 ml). The extract is dried over MgSO4, filtered, then evaporated to yield 14.7 g (79 %) of a yellow viscous oil.

Workup

  1. stirringThe resulting white suspension is stirred for a further 30 minutes at 10° C.
  2. customUpon reaching ambient temperature
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux
  5. temperaturemaintained at this temperature for 3 hours
  6. temperatureThe reaction mixture is then cooled to 5° C.
  7. temperatureto warm to ambient temperature
  8. temperatureis then heated
  9. temperatureto reflux
  10. temperaturemaintained at this temperature for 2 hours
  11. temperatureThe reaction mixture is cooled to ambient temperature
  12. customthe solvent removed under reduced pressure
  13. extractionThe acidified aqueous suspension is then extracted with either (200 ml)
  14. extractionthe ether extract
  15. washis washed with water (3×50 ml)
  16. dry with materialThe extract is dried over MgSO4
  17. filtrationfiltered
  18. customevaporated

Sources & evidence

ORD record
ord-043277330df84e5c906f026bc99bbdc0
Source dataset
uspto-grants-1990_06
Patent number
US04931196

Linked notes

Loading…