Sodium Hydroxide → HCID 58033225, compound

HRID 712176Notes

Reaction equation

HRID 712176 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH:11]C(=O)C2C=CC=CC=2)=[S:10])[CH:5]=[C:4]([Br:20])[N:3]=1.[OH-].[Na+].CCOC(C)=O.CCCCCC>C1COCC1.CO.O>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[C:4]([Br:20])[N:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 58033240HCID 58033240, compound

Product 1

HCID 58033225HCID 58033225, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2,6-dibromopyridin-4-ylcarbamothioyl)benzamide (14.50 g, 34.93 mmol) in a mixture of THF (600 mL) and MeOH (200 mL) was added a solution of NaOH (7.0 g, 174.65 mmol) dissolved in 200 mL of water. The mixture was heated to 70° C. for 16-22 h. After reaction, the solvent wad distilled under reduced pressure, water added and extracted with EtOAc (3×500 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue thus obtained was treated with 20% EtOAc-hexane and finally filtered to obtain the desired product as an off-white solid (9.0 g, 83%).

Workup

  1. customAfter reaction
  2. distillationthe solvent wad distilled under reduced pressure, water
  3. additionadded
  4. extractionextracted with EtOAc (3×500 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. filtrationfinally filtered

Sources & evidence

ORD record
ord-59823367c329461c96bcdb6a90d1ea43
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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