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Tetrahydrofuran → 2-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanthioamide

HRID 1655542
Notes
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Reaction equation

HRID 1655542 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:35]=[CH:34][C:16]([O:17][CH:18]([CH3:33])[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=O)=[CH:15][CH:14]=1)[CH:6]=[N:5]2.C1COCC1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:42]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:35]=[CH:34][C:16]([O:17][CH:18]([CH3:33])[C:19](=[S:42])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[CH:15][CH:14]=1)[CH:6]=[N:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14817Phosphorus sulfide (P2S5)HCID 197926992-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

Product 1

HCID 197926792-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanthioamide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

A mixture of 2.0 g (4.1 mmol) of 2-(4-((6-fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide and 40 ml of dry THF in a 100 ml flask was placed in a water-filled ultrasonic bath. Phosphorous pentasulfide (0.22 g) was added and the mixture sonicated while maintaining the reaction temperature below 40° C. by occasional addition of ice to the water bath. Additional P2S5 (1.76 g) was added in portions at 20 minute intervals over the next hour. Sonication was continued for an additional 2 hours and the mixture then filtered and the solid washed well with methylene chloride. The combined filtrates were treated with charcoal, filtered and evaporated to dryness. The residue was purified first by chromatography over silica gel, eluting with CH2Cl2, and then by preparative scale HPLC, eluting with 85:15 hexane: acetone. This left 1.1 g (53 percent of theoretical) of the above-named product as a yellow glassy solid. (Compound 34)

Workup

  1. additionfilled ultrasonic bath
  2. customthe mixture sonicated
  3. temperaturewhile maintaining the reaction temperature below 40° C.
  4. customSonication
  5. filtrationthe mixture then filtered
  6. washthe solid washed well with methylene chloride
  7. additionThe combined filtrates were treated with charcoal
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified first by chromatography over silica gel
  11. washeluting with CH2Cl2
  12. washby preparative scale HPLC, eluting with 85:15 hexane

Sources & evidence

ORD record
ord-91b9e493e41d49a4b0a84f1c7bd934bf
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05250690

Reaction notes

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