Ammonium Chloride → HCID 21644471, compound

HRID 1033830Notes

Reaction equation

HRID 1033830 reaction equation
C([S:8][C:9]([CH2:22][O:23][CH3:24])([CH2:19][O:20][CH3:21])[CH2:10][N:11]([CH2:13][CH2:14][P:15]([CH3:18])([CH3:17])=S)[CH3:12])C1C=CC=CC=1.[Na].[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:18][P:15]([CH3:17])[CH2:14][CH2:13][N:11]([CH2:10][C:9]([CH2:19][O:20][CH3:21])([CH2:22][O:23][CH3:24])[SH:8])[CH3:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 19024936HCID 19024936, compound

Product 1

HCID 21644471HCID 21644471, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

A solution of 2-benzylthio-N-(2-dimethylphosphinothioylethyl)-3-methoxy-2-methoxymethyl-N-methylpropylamine (450 mg) in dry tetrahydrofuran (10 cm3) was placed in a flask fitted with a low temperature condenser (-50° C.), drying tube and gas inlet. The flask was flushed with nitrogen, the solution cooled to -50° C., and then dry ammonia (40 cm3) was condensed into the flask. Small pieces of sodium were then added to this mixture until the blue colouration persisted for at least 1 hour. The blue colouration was then discharged by the addition of ammonium chloride, and the mixture allowed to warm to room temperature. As the ammonia evaporated steps were taken to ensure that no air entered the apparatus. [The flask and its contents were then transfered to a glove box containing a nitrogen atmosphere for subsequent operations.] The reaction mixture was then filtered and the solvent removed under reduced pressure to give a yellow oil containing some solid material. The oil was dissolved in chloroform, the solid removed by filtration, and the solvent removed under reduced pressure to give 2-[N-(2-dimethylphosphinoethyl)-N-methylamino]-1,1-bis(methoxymethyl)ethanethiol as a white solid.

Workup

  1. customfitted with a low temperature condenser (-50° C.)
  2. customdrying tube and gas inlet
  3. customThe flask was flushed with nitrogen
  4. customcondensed into the flask
  5. waitpersisted for at least 1 hour
  6. temperatureto warm to room temperature
  7. customAs the ammonia evaporated steps
  8. custom[The flask and its contents were then transfered to a glove box
  9. additioncontaining a nitrogen atmosphere for subsequent operations
  10. filtration] The reaction mixture was then filtered
  11. customthe solvent removed under reduced pressure
  12. customto give a yellow oil
  13. additioncontaining some solid material
  14. customthe solid removed by filtration
  15. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c5bdf2a8d5ae4fe793a340acd96e3832
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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