Ammonium Chloride → HCID 58474870, compound

HRID 1400928Notes

Reaction equation

HRID 1400928 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][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:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Zn]>[F:1][C:2]1[CH:29]=[C:28]([CH:27]=[CH:26][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:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[CH:18]=3)[S:13][C:6]=12)[NH2:30]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474557HCID 58474557, compound

Product 1

HCID 58474870HCID 58474870, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 360 (150 mg, 0.329 mmol) in MeOH (10 mL) was added ammonium chloride (35.3 mg, 2 eq, 0.660 mmol) in water (1 mL) and zinc powder (86 mg, 4 eq, 1.320 mmol) and the reaction mixture was heated to reflux for 3 hours. The mixture was cooled to RT then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM and washed with water. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound 361 (98 mg, 70% yield) that was used in the next step with no additional purification. MS (m/z): 425.5 (M+H)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationthen filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  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-784a7ad17f834ff89d6fa25bd8bbc550
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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