Sodium Thiosulfate → HCID 68606931, compound

HRID 2065735Notes

Reaction equation

HRID 2065735 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[Cl:11].[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([Br:13])=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[Cl:11]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 5200412Methyl 5-Amino-2-chlorobenzoateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 68606931HCID 68606931, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-amino-2-chloro-benzoic acid methyl ester (6.76 g, 36.4 mmol) in dichloromethane (100 mL) and methanol (50 mL) was added tetra-n-butylammonium tribromide (17.7 g, 36.4 mmol). The mixture was stirred at 25° C. for 90 minutes. Sodium thiosulfate (10% aqueous solution) was added and the mixture was extracted with dichloromethane. The combined extracts were washed with water, dried (Na2SO4), filtered, and concentrated to dryness under reduced pressure. The crude material was purified by flash column chromatography (hexane/acetone 8:2). Fractions with the desired product were concentrated to small volume. The resulting suspension was allowed to stand for two hours and was then filtered to obtain 5-amino-6-bromo-2-chloro-benzoic acid methyl ester as a white solid (2.7 g, 28%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude material was purified by flash column chromatography (hexane/acetone 8:2)
  7. concentrationFractions with the desired product were concentrated to small volume
  8. waitto stand for two hours
  9. filtrationwas then filtered

Sources & evidence

ORD record
ord-019d505be7c3401e86ca3cc3e505a230
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

Loading…