Water → HCID 13365750, compound

HRID 1074437Notes

Reaction equation

HRID 1074437 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:28])[CH2:6][N:7]([C:9]([C:11]1[C:20]2[C:15](=[C:16]([S:23][C:24]([F:27])([F:26])[F:25])[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[S:10])[CH3:8].O>COCCO>[CH3:22][O:21][C:17]1[C:16]([S:23][C:24]([F:26])([F:25])[F:27])=[C:15]2[C:20](=[CH:19][CH:18]=1)[C:11]([C:9](=[S:10])[N:7]([CH3:8])[CH2:6][C:5]([OH:28])=[O:4])=[CH:12][CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14391173HCID 14391173, compound

Product 1

HCID 13365750HCID 13365750, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Aqueous NaOH (3.41 mL, 2 N) was added to a solution of N-[[6-methoxy-5-(trifluoromethylthio)-1-naphthalenyl]thioxomethyl]-N-methylglycine methyl ester (1.375 g, 3.4 mmoles) in 2-methoxyethanol (20 ml). The solution was stirred at 20°-22° C. for 4 hr. Water was added and the cloudy mixture was extracted with ethyl acetate. The aqueous layer was made acidic (pH=3) with 1 N aqueous HCl and extracted with ethyl acetate. The latter extract was washed successively with water and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from chloroform-hexane to give the title compound (672 mg); mp 168°-169° C.; NMR (DMSO-d6) δ 3.0 (s, 3H), 4.0 (s, 3H), 4.6 and 5.2 (d, J=16.5 Hz, 2H), 7.7 (m, 5H); ir (white mineral oil) 2900, 1720, 1465 cm-1 ; uvλmax (MeOH) 342 nm (ε4970), 334 (4800), 230 (46,800).

Workup

  1. extractionthe cloudy mixture was extracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. extractionThe latter extract
  4. washwas washed successively with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-c705dfe3791d48d6a1acc6fd7351847a
Source dataset
uspto-grants-1983_07
Patent number
US04391825

Reaction notes

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