Ammonium Chloride → HCID 58474436, compound

HRID 1400832Notes

Reaction equation

HRID 1400832 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][C:22]4=[O:27])=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CO.O.[Zn]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:19]=[CH:18][C:17]([CH2:20][N:21]5[CH2:26][CH2:25][O:24][CH2:23][C:22]5=[O:27])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:31]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474761HCID 58474761, compound

Product 1

HCID 58474436HCID 58474436, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 121 (135 mg, 0.281) in MeOH (10 mL) was added Zinc powder (184 mg, 2.81 mmol) and NH4Cl (60.1 mg, 1.124 mmol) in water (1 mL) and the reaction mixture was stirred at reflux for 5 hours then stirred at RT for 2 days. The mixture was filtered, concentrated, dissolved in DCM and MeOH and the resultant solution was then washed with water. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid 122 (65 mg, 51% yield) was used directly in the next step with no additional purification. MS (m/z)=451.49 (M+H)

Workup

  1. temperatureat reflux for 5 hours
  2. stirringthen stirred at RT for 2 days
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. dissolutiondissolved in DCM
  6. washMeOH and the resultant solution was then washed with water
  7. customThe organic phase was collected
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c3758e72bcac440ba68d0285c492286c
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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