Water → HCID 86613173, compound

HRID 746789Notes

Reaction equation

HRID 746789 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[CH:21][C:22]=2[NH:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:14][CH:13]=1)#[N:2].Cl[Sn]Cl.O>C(O)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][CH:20]=[CH:21][C:22]=3[NH:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:14][CH:13]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 86613174HCID 86613174, compound2×

Product 1

HCID 86613173HCID 86613173, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Prepare propane-2-sulfonic acid [2-(2′-cyano-5′-nitro-biphenyl-4-yl)-thiophen-3-yl]-amide in a manner analogous to the procedure set forth in Preparation 4. Add SnCl2.2 H2O (642 mg, 3.40 mmol) into a solution of propane-2-sulfonic acid [2-(2′-cyano-5′-nitro-biphenyl-4-yl)-thiophen-3-yl]-amide (279 mg, 0.654 mmol) in ethanol (6.54 mL). Heat the mixture at 90° C. for 3 h. Cool to room temperature. Concentrate to remove the solvent in vacuo. Dilute with dichloromethane, and add aqueous sodium bicarbonate solution to adjust pH to 8. Extract with with dichloromethane (3×100 mL) and dry the combined organic layers and concentrate to give a slightly colored solid. Purification by flash chromatography (Silica gel-Hexane/EtOAc 2:1) furnishes 212 mg, 0.534 mmol (82%) of title compound as a pale yellow solid. MS (m/e): 396.1 (M−1).

Workup

  1. customset forth in Preparation 4
  2. temperatureCool to room temperature
  3. concentrationConcentrate
  4. customto remove the solvent in vacuo
  5. additionDilute with dichloromethane
  6. additionadd aqueous sodium bicarbonate solution
  7. extractionExtract with with dichloromethane (3×100 mL)
  8. customdry the combined organic layers
  9. concentrationconcentrate
  10. customto give a slightly colored solid
  11. customPurification by flash chromatography (Silica gel-Hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-30a1d16a5c0d401786ea9446626c3999
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

Loading…