Stannous chloride dihydrate → HCID 10465412, compound

HRID 1600731Notes

Reaction equation

HRID 1600731 reaction equation
[Na+].[Cl:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([NH:10][CH2:11][C:12]([O-])=[O:13])=[C:5]([N+:15]([O-])=O)[CH:4]=1.[Na+].ClC1C=C([N+]([O-])=O)C(F)=CC=1NCC([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:6]([NH:10][CH2:11][C:12](=[O:13])[NH:15]2)=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21189997HCID 21189997, compoundHCID 21190009HCID 21190009, compound

Product 1

HCID 10465412HCID 10465412, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of a mixture of N-(4'-chloro-5'-fluoro-2'-nitrophenyl)glycine sodium salt and N-(2'-chloro-5'-fluoro-4'-nitrophenyl)glycine sodium salt (0.175 g, 0.704 mmol, as prepared above) and tin (II) chloride dihydrate (0.475 g, 2.11 mmol, Aldrich, used as received) in ethanol (3.5 mL) was refluxed for 30 min. It was then cooled to room temperature and the solvent was removed under vacuum. The residue was diluted with water (10 mL) and basified with saturated NaHCO3 (3.0 mL) to pH~8. The resulting white suspension was extracted with ethyl acetate (30 mL). The ethyl acetate was dried over anhydrous Na2SO4 and removed under vacuum to yield 0.041 g (29%) of the pure (1H NMR) title compound as a light yellow powder; m.p. 217-219° C. (decomposed); 1H NMR (DMSO-d6): δ 3.745 (s, 2H), 6.37 (s, 1H), 6.587 (d, 1H, J=10.5 Hz), 6.741 (d, 1H, J=7.2 Hz), 10.331 (s, 1H).

Workup

  1. temperaturewas refluxed for 30 min
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water (10 mL)
  4. extractionThe resulting white suspension was extracted with ethyl acetate (30 mL)
  5. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  6. customremoved under vacuum

Sources & evidence

ORD record
ord-676154ab390f46e498505238e81845ec
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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