Hydrochloric Acid → HCID 45158995, compound

HRID 2044133Notes

Reaction equation

HRID 2044133 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17].NC(N)=[S:24].[OH-].[Na+].Cl>O>[SH:24][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 11773557HCID 11773557, compound

Product 1

HCID 45158995HCID 45158995, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In the second step, diethyl 12-bromododecylphosphonate (20.01 g; 51.9 mmol) is reacted, under an inert atmosphere, with thiourea (4 g; 51.9 mmol) in 200 ml of water at 100° C. with stirring for 12 hours. After cooling, a solution of sodium hydroxide (2.07 g; 51.9 mmol) in 100 ml of water is added dropwise and the reaction mixture is refluxed for 3 hours. After cooling to room temperature, hydrochloric acid solution (32%) is added dropwise to pH 1. The solution is then stirred for 24 hours. The organic phase is then recovered with 100 ml of CH2Cl2, washed with distilled water, dried over sodium sulfate, filtered and evaporated under reduced pressure. The yellow oil obtained is purified by chromatography on a column of silica gel (eluent: hexane/8% EtOAc) to give 10.8 g (n=38.16 mmol) of diethyl 12-mercaptododecylphosphonate (52% yield).

Workup

  1. temperatureAfter cooling
  2. temperaturethe reaction mixture is refluxed for 3 hours
  3. stirringThe solution is then stirred for 24 hours
  4. customThe organic phase is then recovered with 100 ml of CH2Cl2
  5. washwashed with distilled water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe yellow oil obtained
  10. customis purified by chromatography on a column of silica gel (eluent: hexane/8% EtOAc)

Sources & evidence

ORD record
ord-dd960a2154a74d4782836b82aba0bb14
Source dataset
uspto-grants-2013_11
Patent number
US08586758B2

Reaction notes

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