Water → HCID 18427791, compound

HRID 1279281Notes

Reaction equation

HRID 1279281 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[NH:22][NH2:23].O>CCOCC.C(N(CC)CC)C.C(Cl)Cl>[C:1]([CH2:3][C:4]([N:22]([C:15]1[C:16]([Cl:21])=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=1[Cl:13])[NH2:23])=[O:6])#[N:2]

Participants

8

Reactant 4

HCID 962WaterHCID 9740Cyanoacetic acidHCID 24819Phosphorus pentachloride2×HCID 79234(2,4,6-Trichlorophenyl)hydrazine

Product 1

HCID 18427791HCID 18427791, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Cyanoacetic acid (8.5 g, 0.10 mol) in 200 mL of dry ether was treated with 20.8 g (0.10 mol) of phosphorous pentachloride, warmed briefly to reflux and let cool to room temperature at which time all of the phosphorous pentachloride, had dissolved. After a small amount of insoluble material was removed by filtration, the ether was removed on the rotary evaporator. Then 100 mL of toluene was added and stripped to remove phosphorous oxytrichloride. The residual pale yellow oil was immediately dissolved in 50 mL of cold methylene dichloride and added to a cold suspension of 21.15 g (0.10 mol) of 2,4,6-trichlorophenylhydrazine in 14.0 mL of triethylamine and 100 mL of methylene dichloride, keeping the temperature below 20° C. by use of an ice bath. The reaction mixture was allowed to warm to room temperature and stirred for one hour. Then 500 mL of cold water was added. The precipitated solid was filtered and washed with water and with a little methylene dichloride to give the intermediate 2-cyano-N-(2,4,6-trichlorophenyl)acethydrazide, 14.92 g (54%), m.p. 166-168° C.

Workup

  1. temperaturewarmed briefly
  2. temperatureto reflux
  3. dissolutionhad dissolved
  4. customAfter a small amount of insoluble material was removed by filtration
  5. customthe ether was removed on the rotary evaporator
  6. additionThen 100 mL of toluene was added
  7. customto remove phosphorous oxytrichloride
  8. dissolutionThe residual pale yellow oil was immediately dissolved in 50 mL of cold methylene dichloride
  9. customthe temperature below 20° C.
  10. filtrationThe precipitated solid was filtered
  11. washwashed with water and with a little methylene dichloride

Sources & evidence

ORD record
ord-52663fe73d8f435ebd8c9c27ce9e67a8
Source dataset
uspto-grants-2002_09
Patent number
US06448265B1

Reaction notes

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