Phosphorus oxychloride → HCID 18183181, compound

HRID 1359574Notes

Reaction equation

HRID 1359574 reaction equation
[NH:1]([CH2:5][C:6]1[CH2:12][C:11]2[CH:13]=[C:14]3[O:19][CH2:18][O:17][C:15]3=[CH:16][C:10]=2[C:9]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[N:8][N:7]=1)[C:2]([CH3:4])=O.P(Cl)(Cl)(Cl)=O>C(Cl)Cl>[CH3:4][C:2]1[N:7]2[N:8]=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)[C:10]3[CH:16]=[C:15]4[O:17][CH2:18][O:19][C:14]4=[CH:13][C:11]=3[CH2:12][C:6]2=[CH:5][N:1]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18183126HCID 18183126, compound

Product 1

HCID 18183181HCID 18183181, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.40 g (1.05 mmol) of the acetamido compound of step C is suspended in 20 ml of methylene chloride and mixed with 0.48 ml (5.3 mmol) of phosphorus oxychloride. Then, the mixture is heated to boiling for 3 hours. After concentration by evaporation, the residue is taken up in methylene chloride (30 ml) and washed with sodium bicarbonate solution and water, dried, filtered and concentrated by evaporation. 0.38 g of solid substance, which is purified by column chromatography, is obtained (silica gel, eluant chloroform:methanol=95:5). 0.32 g (84%) of pure title compound with a melting point of 305-310° C. (decomposition) is obtained.

Workup

  1. temperatureThen, the mixture is heated
  2. concentrationAfter concentration
  3. customby evaporation
  4. washwashed with sodium bicarbonate solution and water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. custom0.38 g of solid substance, which is purified by column chromatography
  9. customis obtained (silica gel, eluant chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-aff452da60344f0e81d7ddf2d5a8cdb5
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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