Thiazolidine → O,S-Dimethyl (3-Thiazolidinylcarbonyl)phosphoramidothioate

HRID 1461229Notes

Reaction equation

HRID 1461229 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][CH2:2]1.[P:6](=[O:14])([N:11]=[C:12]=[O:13])([S:9][CH3:10])[O:7][CH3:8]>CCOCC>[S:1]1[CH2:5][CH2:4][N:3]([C:12]([NH:11][P:6](=[O:14])([S:9][CH3:10])[O:7][CH3:8])=[O:13])[CH2:2]1

Participants

4

Reactant 2

HCID 10444ThiazolidineHCID 14879948O,S-dimethyl phosphoroisocyanatidothioate

Product 1

HCID 57269176O,S-Dimethyl (3-Thiazolidinylcarbonyl)phosphoramidothioate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.45 g of thiazolidine in 100 ml of ether was cooled to about 0° C. and 8.35 g of O,S-dimethyl phosphoroisocyanatidothioate was added dropwise with stirring. The mixture was allowed to warm to ambient temperature and react for about 1 hour at which time the precipitate that formed was collected by filtration. This precipitate was then recrystallized from a small amount of 2-propanol to obtain 3.6 g (28 percent of theory) of the title compound as white crystals melting at 84°-86° C.

Workup

  1. customreact for about 1 hour at which time the precipitate
  2. customthat formed
  3. filtrationwas collected by filtration
  4. customThis precipitate was then recrystallized from a small amount of 2-propanol

Sources & evidence

ORD record
ord-e8194d1cd3714fa089ab9a12a5fef8d0
Source dataset
uspto-grants-1991_12
Patent number
US05075293

Reaction notes

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