Benzene → HCID 13745836, compound

HRID 620725Notes

Reaction equation

HRID 620725 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:25]=[CH:24][C:13]([C:14]([N:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].C1C=CC=CC=1.Cl>O.N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:25]=[CH:24][C:13]([C:14]([N:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[S:27])=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 14817Phosphorus sulfide (P2S5)HCID 13745829HCID 13745829, compound

Product 1

HCID 13745836HCID 13745836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A suspension of 0.40 g of 4-diethoxyphosphinylmethyl-N-methyl-N-phenylbenzamide and 0.56 g of phosphorus pentasulfide in a mixed solvent of 20 ml of dry benzene and 5 ml of dry pyridine was refluxed for 7 hours. After being allowed to cool to room temperature, the reaction mixture was poured into 50 ml of ice water. The water layer was made acidic with 4N hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (eluent; benzene:ethyl acetate=1:1) to give 4-diethoxyphosphinylmethyl-N-methyl-N-phenylthiobenzamide. Recrystallization from benzene-n-hexane gave 0.23 g of yellow needles.

Workup

  1. temperaturewas refluxed for 7 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f72efe45779434c9e3556f47ce4edd9
Source dataset
uspto-grants-1989_04
Patent number
US04822780

Reaction notes

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