Phosphorus pentachloride → HCID 53839116, compound

HRID 1704609Notes

Reaction equation

HRID 1704609 reaction equation
[C:1]([NH:4][N:5]=[C:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:18].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:10]([O:9][C:7]([C:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[N:5][N:4]=[C:1]([Cl:18])[CH3:2])=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 86736174HCID 86736174, compound

Product 1

HCID 53839116HCID 53839116, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

240 g (1 mol) of thien-2-yl-glyoxylic acid ethyl ester 2-acetylhydrazone were dissolved in 1,000 ml of methylene chloride and 208 g (1 mol) of phosphorus pentachloride were added at -10° to 0° C. Stirring was continued for half an hour, ice-water was added to the reaction mixture and the batch was neutralised with sodium bicarbonate solution. The organic phase was separated off, dried over sodium sulphate and concentrated by distilling off the solvent. 234 g (0.92 mol) of crude 1-ethoxycarbonyl-4-chloro-4-methyl-1-thien-2-yl-2,3-diazabutadiene were obtained as an oil which would be directly reacted further. ##STR11##

Workup

  1. waitwas continued for half an hour
  2. customThe organic phase was separated off
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-77ff2df561e747849089801da9f91485
Source dataset
uspto-grants-1978_11
Patent number
US04127404

Reaction notes

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