Ammonium Chloride → HCID 58474361, compound

HRID 1400847Notes

Reaction equation

HRID 1400847 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[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Zn]>[F:1][C:2]1[CH:31]=[C:30]([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[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]4)[CH:18]=3)[S:13][C:6]=12)[NH2:32]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474929HCID 58474929, compound

Product 1

HCID 58474361HCID 58474361, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 152 (150 mg, 0.311 mmol) in MeOH (20 mL) was added ammonium chloride (33.3 mg, 0.622 mmol) in water (5 mL) and zinc powder (81 mg, 3.01 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 title compound 153 (132 mg, 92% yield) that was used directly in the next step with no additional purification. MS (m/z)=453.2 (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-07445b9bb190473caa0b2447e95b5b2f
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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