Thiophenol → HCID 54085838, compound

HRID 1448427Notes

Reaction equation

HRID 1448427 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[F:6][C:7]([F:25])([F:24])[C:8]([N:10]([CH2:17][P:18]([O:22]Cl)([O:20]Cl)=[O:19])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9].[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>CCOCC>[F:6][C:7]([F:25])([F:24])[C:8]([N:10]([CH:17]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[P:18]([OH:22])([O:20][S:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:19])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8021DiethylamineHCID 8471TriethylamineHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 54085838HCID 54085838, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of diethylamine (5.0 ml, 0.05 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (8.25 g, 0.025 mole) in 150 ml. of ether at 0° C. The solution was stirred for two hours, then filtered and the filtrate treated with a solution of thiophenol (2.4 ml, 0.025 mole) and triethylamine (3.4 ml, 0.025 mole) in 50 ml. of ether at 0° C. After stirring overnight, the solution was filtered and the filtrate was washed with 0.3% aqueous hydrochloric acid, dried over sodium sulfate and concentrated in vacuo to yield ethyl N-trifluoroacetyl-N-(diethylamino(phenylthio)phosphonomethyl)glycinate (8.7 g) as a yellow oil, ND22 =1.5049.

Workup

  1. customat 0° C
  2. filtrationfiltered
  3. customat 0° C
  4. stirringAfter stirring overnight
  5. filtrationthe solution was filtered
  6. washthe filtrate was washed with 0.3% aqueous hydrochloric acid
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bae4beb6caa41d2b852d5af98aa41b0
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

Loading…