Hydrochloric Acid → 4-oxo-5-phenyl-4H-pyran-2-carbonitrile

HRID 1902654Notes

Reaction equation

HRID 1902654 reaction equation
[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][O:5][C:4]([C:14]([NH2:16])=O)=[CH:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C(N(CC)CC)C>[O:1]=[C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][O:5][C:4]([C:14]#[N:16])=[CH:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 11776TriphenylphosphineHCID 130911764-oxo-5-phenyl-4H-pyran-2-carboxamide

Product 1

HCID 130911754-oxo-5-phenyl-4H-pyran-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of this amide (3.5 g) and triphenylphosphine (8.54 g) in carbon tetrachloride (10 ml), methylene chloride (20 ml) and triethylamine (2.3 ml) was stirred for 4 hours at room temperature. Ice (60 g) and 2 N hydrochloric acid (30 ml) were added, followed by sufficient chloroform to dissolve all the solid material. The solvent layer was washed with water, dried and evaporated, and the residue was crystallised from chloroform-petroleum spirit (60°-80° C.) and then from ethanol to give the title product (mp 177°-179° C.).

Workup

  1. dissolutionto dissolve all the solid material
  2. washThe solvent layer was washed with water
  3. customdried
  4. customevaporated
  5. customthe residue was crystallised from chloroform-petroleum spirit (60°-80° C.)

Sources & evidence

ORD record
ord-ba388d837ca34a909bc0ed652bc4d460
Source dataset
uspto-grants-1982_12
Patent number
US04364956

Reaction notes

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