Toluene → 2-Thioxo-2-ethoxy-5-methyl-1,3,2-oxazaphospholane

HRID 2166503Notes

Reaction equation

HRID 2166503 reaction equation
[S:1]=[P:2]1(Cl)[NH:6][CH2:5][CH:4]([CH3:7])[O:3]1.C1(C)C=CC=CC=1.[CH3:16][CH2:17][O-:18].[Na+]>C(O)C>[S:1]=[P:2]1([O:18][CH2:17][CH3:16])[NH:6][CH2:5][CH:4]([CH3:7])[O:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 2723922Sodium ethoxideHCID 127603172-Thioxo-2-chloro-5-methyl-1,3,2-oxazaphospholane

Product 1

HCID 127603182-Thioxo-2-ethoxy-5-methyl-1,3,2-oxazaphospholaneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

18 g (0.1 mol) of 2-thioxo-2-chloro-5-methyl-1,3,2-oxazaphospholane were initially introduced into 100 ml of toluene, and a solution of 0.1 mol of sodium ethylate in ethanol was added dropwise at an internal temperature of between 10° and 15° C. The reaction mixture was stirred for a further two hours, washed with water, dried and filtered and the filtrate was distilled. 15 g (83% of theory) of 2-thioxo-2-ethoxy-5-methyl-1,3,2-oxazaphospholane were obtained as a colorless liquid of boiling point 78° C./0.01 mbar and of refractive index nD23 : 1.5041.

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-54a986938c6044e98772a76c03b3b49f
Source dataset
uspto-grants-1983_06
Patent number
US04387060

Reaction notes

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