Phosphorus oxychloride → HCID 21430649, compound

HRID 437201Notes

Reaction equation

HRID 437201 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][CH:7]([CH2:24][O:25][C:26]1[C:31]2[C:32](=[O:39])[CH:33]=[C:34]([C:36]([NH2:38])=O)[O:35][C:30]=2[CH:29]=[CH:28][CH:27]=1)[CH2:8][O:9][C:10]1[C:15]2[C:16](=[O:23])[CH:17]=[C:18]([C:20]([NH2:22])=O)[O:19][C:14]=2[CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[Cl:6][CH:7]([CH2:8][O:9][C:10]1[C:15]2[C:16](=[O:23])[CH:17]=[C:18]([C:20]#[N:22])[O:19][C:14]=2[CH:13]=[CH:12][CH:11]=1)[CH2:24][O:25][C:26]1[C:31]2[C:32](=[O:39])[CH:33]=[C:34]([C:36]#[N:38])[O:35][C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21430652HCID 21430652, compound

Product 1

HCID 21430649HCID 21430649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 120 parts of N,N-dimethylformamide was slowly added 5 parts of phosphorous oxychloride with stirring and ice-cooling. Then 10 parts of 5,5'-[(2-chlorotrimethylene) dioxy]bis[4-oxo-4H-1-benzopyran-2-carboxamide] were added to the solution, in small quantities, and the reaction mixture was stirred at room temperature for 60 hours. The resulting dark solution was poured into 500 parts of ice/water and the precipitated solid was filtered, washed with water and dried to give 6.8 parts of a brown powder. Crystalisation of this product from a mixture of ethanol and N,N-dimethylformamide gave 4.6 parts of 5,5'-[(2-chlorotrimethylene)dioxy]bis[4-oxo-4H-1-benzopyran-2-carbonitrile] as white crystals, m.p. 185° C. (decomp.), giving a positive Beilstein's halogen test.

Workup

  1. temperatureice-cooling
  2. stirringthe reaction mixture was stirred at room temperature for 60 hours
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried
  6. customto give 6.8 parts of a brown powder
  7. customCrystalisation of this product
  8. additionfrom a mixture of ethanol and N,N-dimethylformamide

Sources & evidence

ORD record
ord-4b41daf9edbe4eab89794e30c0e6ee88
Source dataset
uspto-grants-1977_06
Patent number
US04029802

Reaction notes

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