Sodium Carbonate → HCID 20262902, compound

HRID 464315Notes

Reaction equation

HRID 464315 reaction equation
[ClH:1].[CH:2]1([CH2:8][N:9]2[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18]CC)=O)[CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[ClH:1].[CH:2]1([CH2:8][N:9]2[CH2:14][CH2:13][C:12]3[S:28][C:25]4[CH:26]=[CH:27][C:22]([F:21])=[CH:23][C:24]=4[C:16](=[O:18])[C:11]=3[CH2:10]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 677894-FluorothiophenolHCID 20262900HCID 20262900, compound

Product 1

HCID 20262902HCID 20262902, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.68 g of the product of Step B and 2.51 g of p-fluoro-thiophenol were added in two portions with stirring over 20 minutes to 80 g of polyphosphoric acid heated to 100° to 120° C. and the mixture was held at 110° C. for two hours to form a yellow solution which was poured into 500 ml of water. The resulting suspension was adjusted to a pH of 8 by addition of sodium carbonate and the yellow precipitate formed was recovered by filtration. The product was washed with water and dissolved in 250 ml of dichloromethane. The solution was washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and ethanol and 10 ml of a solution of 10% hydrogen chloride in ethanol were added thereto. The mixture was filtered and the pale cream colored product was washed with a little ethanol and dried under reduced pressure to obtain 2.73 g (39 % yield) of 2-cyclohexylmethyl-8-fluoro-1,2,3,4-tetrahydro-10H-(1)-benzothiopyrano[3,2-c]pyridin-10-one hydrochloride melting at 243° C. (decomp.).

Workup

  1. additionwere added in two portions
  2. temperatureheated to 100° to 120° C.
  3. customto form a yellow solution which
  4. customthe yellow precipitate formed
  5. filtrationwas recovered by filtration
  6. washThe product was washed with water
  7. dissolutiondissolved in 250 ml of dichloromethane
  8. washThe solution was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness under reduced pressure
  11. dissolutionThe residue was dissolved in a mixture of ethyl acetate and ethanol and 10 ml of a solution of 10% hydrogen chloride in ethanol
  12. additionwere added
  13. filtrationThe mixture was filtered
  14. washthe pale cream colored product was washed with a little ethanol
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-42ce998690944631aa06158ab8963ce3
Source dataset
uspto-grants-1985_10
Patent number
US04547507

Reaction notes

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