Water → HCID 20399562, compound

HRID 1981366Notes

Reaction equation

HRID 1981366 reaction equation
[C:1]1([C:7]2[S:8](=[O:21])(=[O:20])[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][C:11](=O)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=O)#[N:23].N1C=CC=CC=1.[OH2:36]>C(Cl)(Cl)(Cl)Cl.C1COCC1.Cl[Ti](Cl)(Cl)Cl.CCOCC>[C:14]1([C:9]2[S:8](=[O:21])(=[O:20])[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][C:11](=[CH:29][C:28]([O:27][CH2:25][CH2:24][C:22]#[N:23])=[O:36])[CH:10]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7764Ethyl cyanoacetateHCID 1425134H-Thiopyran-4-one, 2,6-diphenyl-, 1,1-dioxide

Product 1

HCID 20399562HCID 20399562, compound

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.6 ml (0.06 M) of TiCl4 in 15 ml of CCl4 was added dropwise to 120 ml of ice-cooled dry THF (120 ml) under argon. The resulting bright yellow suspension was added quickly to a solution of 8.9 gm (0.03 M) of 2,6-diphenyl-4H-thiopyran-4-one-1,1-dioxide and 3.4 gm (0.03 M) of ethyl cyanoacetate in 70 ml of THF. The mixture was stirred for 20 minutes in the ice-bath. Then 9.5 gm (0.12 M) of dry pyridine was then added. After stirring at room temperature overnight 30 ml of H2O and a small amount of ether was added to the reaction mixture. The organic phase was separated, washed with dilute NaHCO3, brine, dried (MgSO4) and rotavaporated to give 11.4 gm of a highly fluorescent yellow solid. The latter solid was recrystallized from toluene containing a little hexane to give the titled compound (mp 156°-7° C.).

Workup

  1. customThe organic phase was separated
  2. washwashed with dilute NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. customto give 11.4 gm of a highly fluorescent yellow solid
  5. customThe latter solid was recrystallized from toluene containing a little hexane

Sources & evidence

ORD record
ord-7238d0ab6e93471198452bc8b91cc82f
Source dataset
uspto-grants-1985_04
Patent number
US04514481

Reaction notes

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