Stannous chloride dihydrate → HCID 10037490, compound

HRID 1600726Notes

Reaction equation

HRID 1600726 reaction equation
[Br: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.BrC1C=C([N+]([O-])=O)C(F)=CC=1NCC(O)=O.O.O.[Sn](Cl)Cl>C(O)C>[Br: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

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 100857532-[(4-Bromo-5-fluoro-2-nitrophenyl)amino]acetic AcidHCID 10469611N-(2-Bromo-5-fluoro-4-nitrophenyl)glycine

Product 1

HCID 10037490HCID 10037490, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of a mixture of N-(4'-bromo-5'-fluoro-2'-nitrophenyl)glycine and N-(2'-bromo-5'-fluoro-4'-nitrophenyl)glycine (0.150 g, 0.512 mmol, as prepared above) and tin (II) chloride dihydrate (0.346 g, 1.53 mmol, Aldrich, used as received) in ethanol (3.0 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 0.050 g of crude product, which was purified by precipitation from ethanol:water (1:1) to give 30 mg (24%) of the pure (1H NMR) title compound as a light yellow powder; m.p. 172° C. (decomposed); 1H NMR (DMSO-d6): δ 3.73 (s, 2H), 6.37 (s, 1H), 6.551 (d, 1H, J=10.2 Hz), 6.825 (d, 1H, J=6.6 Hz), 10.303 (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
  7. customto yield 0.050 g of crude product, which
  8. customwas purified by precipitation from ethanol:water (1:1)

Sources & evidence

ORD record
ord-c7c7b0872b1840759a1be407e5f43cc9
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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