Pyridine → HCID 131714823, compound

HRID 364447Notes

Reaction equation

HRID 364447 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:22]([F:40])([F:39])[C:23]([F:38])([F:37])[C:24]([F:36])([F:35])[C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:15]([CH3:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=O)=[CH:8][CH:7]=[CH:6]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:42].N1C=CC=CC=1>O>[CH3:1][O:2][C:3]1[C:4]([C:22]([F:40])([F:39])[C:23]([F:38])([F:37])[C:24]([F:36])([F:35])[C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13](=[S:42])[N:15]([CH3:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 131714824HCID 131714824, compound

Product 1

HCID 131714823HCID 131714823, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[[6-methoxy-5-(tridecafluorohexyl)-1-naphthalenyl]carbonyl-N-methylglycine, methyl ester (100 mg, 0.165 mmol), prepared as in Example 5, phosphorus pentasulfide (67 mg) and dry pyridine (2 ml) were refluxed for 2 hours. After stirring overnight at room temperature, the mixture was refluxed for 2 additional hours, poured into water and extracted with ether. The ether extract was washed with 1N aqueous hydrochloric acid, water, saturated sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated giving 92.8 mg of the crude N-[[6-methoxy-5-(tridecafluorohexyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, methyl ester, which was used in the next preparation without further purification. ms: m/e 622 (M+H)+, 562, 519, 503, 352. nmr (CDCl3): δ2.84 & 3.04 (2s, 3H, N--CH3, rotamers); δ3.82 & 3.95 (2s, 3H, O--CH3, rotamers) δ3.4 & 5.5 (2d, 2 H, CH2, J=17); δ7.3 (m, 3H, Har); δ8.2 (m, 2H, Har).

Workup

  1. temperaturewere refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 2 additional hours
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 1N aqueous hydrochloric acid, water, saturated sodium bicarbonate and brine
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-96154fc9a1e2426a974b259d65c4a8ac
Source dataset
uspto-grants-1986_08
Patent number
US04604406

Reaction notes

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