Hydrochloric Acid → HCID 13672317, compound

HRID 364446Notes

Reaction equation

HRID 364446 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13](=[S:21])[N:14]([CH3:20])[CH2:15][C:16]([O:18]C)=[O:17])=[CH:8][CH:7]=[CH:6]2.COCCO.[OH-].[Na+].Cl>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[C:4]([C:22]([F:28])([F:27])[C:23]([F:24])([F:25])[F:26])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13](=[S:21])[N:14]([CH3:20])[CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 131714822HCID 131714822, compound

Product 1

HCID 13672317HCID 13672317, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

The N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, methyl ester (2.3 g, 5.46 mmol), 2-methoxyethanol (50 ml) and 2N aqueous sodium hydroxide (5.46 ml) were mixed at 0° C. and the mixture stirred at room temperature for 3 hours (until disappearance of the ester spot in t.l.c. with ethyl acetate/hexane 1:1). The mixture was cooled to 0° C., neutralized to pH 8 with 1N aqueous hydrochloric acid, evaporated, the residue triturated with water, the neutral material extracted with ethyl acetate and the aqueous layer acidified with 1N aqueous hydrochloric acid to pH3. The product was extracted with ethyl acetate, the extract washed with water, dried over anhydrous MgSO4 and evaporated. The residue was purified by crystallization from chloroform/hexane to obtain 700 mg of the first crop and an additional 568 mg of the crude material from the mother liquor. Recrystallization of the first crop afforded 400 mg of the pure N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine. The recrystallization of mother liquor gave further 291 mg. mp. 164°-165° C. Anal. Calcd: C, 50.13% H, 3.46% N, 3.44% Found: C, 49.42%, H, 3.58% N, 3.40%. nmr (DMSO): δ2.95 (s, 3H, N--CH3); δ3.97 (s, 3H, OCH3); δ4.9 (q, 2H, CH2); δ7.1-8.4 (m, 5H, Har). ir (nujol): 1700, 1723, 1750 cm-1 uv, λmax(ε): 338 (3990), 269 (13,000), 227 (45,400) ms: m/e 407 (M+), 363, 319.

Workup

  1. customevaporated
  2. customthe residue triturated with water
  3. extractionthe neutral material extracted with ethyl acetate
  4. extractionThe product was extracted with ethyl acetate
  5. washthe extract washed with water
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated
  8. customThe residue was purified by crystallization from chloroform/hexane
  9. customto obtain 700 mg of the first crop
  10. customRecrystallization of the first crop

Sources & evidence

ORD record
ord-6c528c577b7d44daa34fb7221227fb2c
Source dataset
uspto-grants-1986_08
Patent number
US04604406

Reaction notes

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