Hydrogen Sulfide → HCID 14391173, compound

HRID 1074436Notes

Reaction equation

HRID 1074436 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([S:21][C:22]([F:25])([F:24])[F:23])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=O)[CH3:6].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:28].O.S>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([S:21][C:22]([F:25])([F:24])[F:23])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[S:28])[CH3:6]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 14391172HCID 14391172, compound

Product 1

HCID 14391173HCID 14391173, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

N-[[6-Methoxy-5-(trifluoromethylthio)-1-naphthalenyl]carbonyl]-N-methylglycine methyl ester (2.0 g, 5.4 mmoles) was dissolved in dry pyridine (40 ml). Phosphorus pentasulfide (2.37 g, 10.7 mmoles) was added to the pyridine solution. The mixture was heated at refluxed for 4 hr and then poured into warm water at 50° to 80° C. (caution: evolution of copious quantities of H2S). The mixture was extracted with ethyl acetate. The extract was washed successively with 3 N aqueous HCl, water, a saturated aqueous solution of NaHCO3, water and brine, dried (MgSO4) and concentrated to dryness. The residue was recrystallized from ethanol-water to give 1.6 g of the title compound; mp 121°-123° C.; NMR (CDCl3) δ 3.00 (s, 3H), 3.75 (s, 3H), 4.00 (s, 3H), 4.35 and 4.5 (d, 2H), 7.0-8.5 (m, 5H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat refluxed for 4 hr
  3. additionpoured
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed successively with 3 N aqueous HCl, water
  6. dry with materiala saturated aqueous solution of NaHCO3, water and brine, dried (MgSO4)
  7. concentrationconcentrated to dryness
  8. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-4e28a26c0d854a67903f6ddc97f5bb22
Source dataset
uspto-grants-1983_07
Patent number
US04391825

Reaction notes

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