N-Methylbenzylamine → HCID 54262334, compound

HRID 371256Notes

Reaction equation

HRID 371256 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:10](Cl)([Cl:13])([Cl:12])=[S:11]>CCOCC>[CH2:1]([N:8]([CH3:9])[P:10]([Cl:13])([Cl:12])=[S:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 19883Thiophosphoryl chloride

Product 1

HCID 54262334HCID 54262334, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-benzyl-N-methylamine (2.81 g, 0.32 mol) in 47 mL of ether was added dropwise with stirring to 78.6 g (0.47 mol) of thiophosphoryl chloride in 375 mL of ether at 0° C. under an argon atmosphere. After the addition was complete, the resultant slurry was stirred for 30 min at 0° C., and then for 1 h at 25° C. The amine hydrochloride was removed by filtration and the solvent was concentrated at reduced pressure to provide 28.5 g (92.5%) of a red colored oil.

Workup

  1. additionAfter the addition
  2. waitfor 1 h at 25° C
  3. customThe amine hydrochloride was removed by filtration
  4. concentrationthe solvent was concentrated at reduced pressure

Sources & evidence

ORD record
ord-66d92b20cda447d9b2c05e8cceb8717c
Source dataset
uspto-grants-1985_07
Patent number
US04530714

Reaction notes

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