Phosphorus sulfide (P2S5) → HCID 19838809, compound

HRID 1639306Notes

Reaction equation

HRID 1639306 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][NH:6][C:7]([C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][NH:6][C:7]([C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[S:27]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 19838828HCID 19838828, compound

Product 1

HCID 19838809HCID 19838809, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 2-[2-{N-(3,4-dichlorobenzyl)-carbamoyl}anilino]acetate (16.3 g), phosphorus pentasulfide (19.0 g) and 1,4-dioxane (320 ml) was refluxed for 1 hour. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel (300 g) eluting with chloroform to give ethyl 2-[2-{N-(3,4-dichlorobenzyl)thiocarbamoyl}anilino]acetate (13.72 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel (300 g)
  5. washeluting with chloroform

Sources & evidence

ORD record
ord-f9d3eeb1c6954e1abd5d2d5c2f010e0d
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

Loading…