Lawesson's reagent → HCID 15239087, compound

HRID 1975394Notes

Reaction equation

HRID 1975394 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:8]([NH2:10])=O)[NH:6][CH:7]=1)#[N:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:20]2)=CC=1>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:8](=[S:20])[NH2:10])[NH:6][CH:7]=1)#[N:2]

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 15239086HCID 15239086, compound

Product 1

HCID 15239087HCID 15239087, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-cyanopyrrole-2-carboxamide (1.35 g, 10.0 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (4.0 g, 9.9 mmol) in toluene is heated at 100° C. for 41/2 hours, diluted with tetrahydrofuran and heated at reflux for 20 minutes. The reaction mixture is then cooled and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 4:1 hexanes/ethyl acetate mixture gives the title product as a yellow solid (0.9 g, mp 253° C. dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 minutes
  3. temperatureThe reaction mixture is then cooled
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-c4b80ffb89b84f31b1466b3116379866
Source dataset
uspto-grants-1994_02
Patent number
US05286742

Reaction notes

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