Stannous chloride dihydrate → HCID 11155728, compound

HRID 1593525Notes

Reaction equation

HRID 1593525 reaction equation
[Cl:1][C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[C:4]([N:6]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5].O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CN(C=O)C.Cl>[NH2:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([N:6]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[C:4](=[O:5])[C:3]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:2]=3[Cl:1])[S:8][C:9]=2[CH:15]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 11168039HCID 11168039, compound

Product 1

HCID 11155728HCID 11155728, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g (3.97 mmol) 2,4-Dichloro-N-(3,4-dimethoxy-phenyl)-N-(6-nitro-benzothiazol-2-yl)-benzamide in 25 ml DMF and 4 ml 1N HCl was treated with 2.24 g tin(II) chloride dihydrate and heated to 80° C. for 4 h. After cooling to room temperature 50 ml saturated NaHCO3 was added and the mixture was extracted with ethyl acetate. The organic phase is treated with decalit and filtered. The organic phase of the filtrate was washed with saturated NaCl, dried with MgSO4, filtered and evaporated to dryness. The residue was purified on reversed phase preparative HPLC eluting with an acetonitrile/water gradient to obtain 536 mg (29%) of the title compound as yellowish amorphous solid. MS (m/e): 474.0 (MH+, 100%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. additionThe organic phase is treated with decalit
  4. filtrationfiltered
  5. washThe organic phase of the filtrate was washed with saturated NaCl
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified on reversed phase preparative HPLC
  10. washeluting with an acetonitrile/water gradient

Sources & evidence

ORD record
ord-873e7dc8da574890b33c0cac803523a4
Source dataset
uspto-grants-2007_11
Patent number
US07297707B2

Reaction notes

Loading…