Ammonium Chloride → HCID 58474497, compound

HRID 1400834Notes

Reaction equation

HRID 1400834 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CO.[Zn]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)=[O:21])=[CH:18][CH:19]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474700HCID 58474700, compound

Product 1

HCID 58474497HCID 58474497, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 125 (1.5 g, 3.24 mmol) in MeOH (60 mL) was added Zinc powder (1.693 g, 25.9 mmol) and NH4Cl (0.346 g, 6.47 mmol) and the reaction mixture was heated to reflux for 5 hours. The mixture was cooled to RT and filtered. The filtrate was concentrated and the residue was dissolved in DCM and washed with water. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated to give title compound 126 (1.3 g, 93% yield) as a brown oil which became a puffy solid after removal of residual solvent in high vacuum. MS (m/z)=434.50 (M+H)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in DCM
  6. washwashed with water
  7. customThe organic phase was collected
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-54d3c3c80c9d40e8909ea3c60fc58e05
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

Loading…