Stannous Chloride → HCID 17755988, compound

HRID 1294075Notes

Reaction equation

HRID 1294075 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])[S:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl>CN(C=O)C>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])[S:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 13699063HCID 13699063, compound2×

Product 1

HCID 17755988HCID 17755988, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (6-(4-nitrophenoxy)benzthiazole-2-yl)carbamate (Intermediate 10E-172.7 mg, 0.5 mmol) in DMF (5 mL) was added SnCl2 (474.0 mg, 2.5 mmol) and stirred at room temperature for 4 days. The mixture was extracted with ethyl acetate, and the organic layer was washed with NaHCO3aq. and dried over Na2SO4 then evaporated to remove solvent. The residue dissolved in small amount of DMF was charged on SCX column chromatography then washed with MeOH then eluted with NH3—MeOH to give the title compound (69.2 mg, 44%): MS m/e 316 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with NaHCO3aq
  3. dry with materialand dried over Na2SO4
  4. customthen evaporated
  5. customto remove solvent
  6. dissolutionThe residue dissolved in small amount of DMF
  7. additionwas charged on SCX column chromatography
  8. washthen washed with MeOH
  9. washthen eluted with NH3—MeOH

Sources & evidence

ORD record
ord-b98815dad858495981f3fd11edf7a81f
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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