HCID 86733163, compound → HCID 53810867, compound

HRID 267856Notes

Reaction equation

HRID 267856 reaction equation
Cl([O-])(=O)(=O)=[O:2].[Cl:6][C:7]([C:13]([C:18]#N)=[CH:14][N:15](C)C)=[N:8][CH:9]=[N+:10]([CH3:12])[CH3:11]>C(#N)C.O>[Cl:6][C:7]([N:8]=[CH:9][N:10]([CH3:12])[CH3:11])=[C:13]([CH:18]=[O:2])[C:14]#[N:15]

Participants

4

Reactant 1

HCID 86733163HCID 86733163, compound

Product 1

HCID 53810867HCID 53810867, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

100 g of N-(3-chloro-4-cyano-5-dimethylamino-2-aza-2,4-pentadienylidene)N,N-dimethylammonium perchlorate are dissolved in a mixture of 400 ml of acetonitrile and 400 ml of water. Stirring is carried out for 6 hours at 20° to 22°C and is followed by double extraction with two 400 ml portions of trichloromethane. Following this the combined trichloromethane phases are extracted twice with two 1000 ml portions of water. The organic phase is dried with Na2SO4 or MgSO4 and reduced in volume by distilling off of the solvent at 30° to 35°C to a quarter of the original volume. After allowing the resultant to stand for one hour in an ice-box at about 0°C, the precipitate is vacuum filtered to yield yellowish crystals. 36 g (61%) of 3-chloro-5-dimethylamino-2-formyl-4-aza-2,4-pentadienenitrile, with a melting point of 144°C (with decomposition), are thus obtained.

Workup

  1. extractionis followed by double extraction with two 400 ml portions of trichloromethane
  2. extractionare extracted twice with two 1000 ml portions of water
  3. dry with materialThe organic phase is dried with Na2SO4 or MgSO4
  4. distillationby distilling off of the solvent at 30° to 35°C to a quarter of the original volume
  5. waitto stand for one hour in an ice-box at about 0°C
  6. filtrationfiltered
  7. customto yield yellowish crystals

Sources & evidence

ORD record
ord-302011a2a24540f2b534d49ad9f72262
Source dataset
uspto-grants-1976_03
Patent number
US03944667

Reaction notes

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