Hydrogen Sulfide → HCID 13318009, compound

HRID 745779Notes

Reaction equation

HRID 745779 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([Br:19])[CH:15]=[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:22].O.S>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([Br:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[S:22])[CH3:6]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 13318008HCID 13318008, compound

Product 1

HCID 13318009HCID 13318009, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of N-[(5-bromo-1-naphthalenyl)carbonyl]-N-methylglycine methyl ester (35.5 g, 106 mmoles, described in Example 2) in dry pyridine (100 ml), phosphorus pentasulfide (44.5 g, 200 mmoles) was added portionwise. The mixture was stirred and refluxed for 1.5 hr. and then poured into a liter of water at 50° to 80° C. (caution: evolution of copious quantities of H2S). The mixture was allowed to cool to 20° to 22° C. (room temperature), filtered and the filtrate was extracted with ethyl acetate. The extract was washed with 1N aqueous HCl solution, brine, a saturated solution of sodium carbonate and brine, dried (MgSO4), filtered and evaporated to dryness. The residue was recrystallized from ethanol-water (4:1) to give the title compound; mp 85°-86° C.; NMR (CDCl3) δ 3.0 (s, 3H), 3.85 (s, 3H), 4.58 & 5.37 (2d, J=17, 2H), 7.1-8.3 (m, 6H); UVλmax (EtOH) 281 nm (ε14,480), 218 (14,480).

Workup

  1. temperaturerefluxed for 1.5 hr
  2. filtrationfiltered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with 1N aqueous HCl solution, brine
  5. dry with materiala saturated solution of sodium carbonate and brine, dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was recrystallized from ethanol-water (4:1)

Sources & evidence

ORD record
ord-243a07d32dac42c5b15501c955aa6906
Source dataset
uspto-grants-1986_07
Patent number
US04600724

Reaction notes

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