Stannous chloride dihydrate → HCID 10465412, compound

HRID 1857449Notes

Reaction equation

HRID 1857449 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][CH2:10][C:11](O)=[O:12])=[C:4]([N+:14]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:9][CH2:10][C:11](=[O:12])[NH:14]2)=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 10243762HCID 10243762, compound

Product 1

HCID 10465412HCID 10465412, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-(4'-chloro-5'-fluoro-2'-nitrophenyl)glycine sodiumsaltand N-(2'-chloro-5'-fluoro-4'-nitrophenyl)glycine sodium salt (0.175 g, 0.704 mmol) and tin (II) chloride dihydrate (0.475 g, 2.11 mmol) 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 the pH was adjusted 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%) pure (1H NMR) title compound as a light yellow powder; mp 217-219° C. (dec); 1H NMR (DMSO-d6) δ 3.75 (s, 2H), 6.37 (s, 1H), 6.59 (d, 1H, J=10.5 Hz), 6.74 (d, 1H, J=7.2 Hz), 10.33 (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-b6607ccd50e346879e05c01698bbc4bc
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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