Hydrochloric Acid → HCID 12846667, compound

HRID 2417942Notes

Reaction equation

HRID 2417942 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[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.C(N(CC)CC)C.Cl>C(Cl)(Cl)(Cl)Cl.ClCCl.C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4]([C:14]#[N:16])=[CH:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 12846664HCID 12846664, compound

Product 1

HCID 12846667HCID 12846667, compound

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-oxo-6-phenyl-4H-pyran-2-carboxamide (4.26 g), triphenylphosphine (10.48 g) and triethylamine (2.8 ml) in carbon tetrachloride (40 ml) and dichloromethane (80 ml) was stirred at room temperature for 4 hours. The reactant slowly dissolved. Dilute hydrochloric acid (1 M, 50 ml) and chloroform (100 ml) were added. The organic layer was separated, washed with water, dried over anhydrous magnesium sulphate, filtered and evaporated. The brown residue was recrystallised twice from carbon tetrachloride to yield the title product as off-white crystals (mp 146°-149° C.).

Workup

  1. dissolutionThe reactant slowly dissolved
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe brown residue was recrystallised twice from carbon tetrachloride

Sources & evidence

ORD record
ord-c137fbdeecde41feb637cc6f6a39ae01
Source dataset
uspto-grants-1984_09
Patent number
US04471129

Reaction notes

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