Ammonium Chloride → HCID 58474845, compound

HRID 1400840Notes

Reaction equation

HRID 1400840 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[N:15]([CH3:26])[C:16]([CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][C:21]4=[O:25])=[CH:17][N:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[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[N:15]([CH3:26])[C:16]([CH2:19][N:20]5[CH2:24][CH2:23][CH2:22][C:21]5=[O:25])=[CH:17][N:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474904HCID 58474904, compound

Product 1

HCID 58474845HCID 58474845, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 135 (125 mg, 0.267 mmol) in MeOH (10 mL) was added zinc powder (140 mg, 2.14 mmol) and ammonium chloride (42.9 mg, 0.80 mmol) in water (1 mL) and the reaction mixture was heated to reflux for 4 hours. The mixture was cooled to RT, filtered and concentrated. The residue was partitioned between water and DCM/MeOH and the organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated to afford title compound 136 (77 mg, 66% yield) that was used crude in the next step with no additional purification. MS (m/z)=438.50 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was partitioned between water and DCM/MeOH
  6. customthe organic phase was collected
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-387cb8dc3405421c8d48048243b1b346
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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