Ammonium Chloride → HCID 58474674, compound

HRID 1400851Notes

Reaction equation

HRID 1400851 reaction equation
[CH:1]1([NH:4][C:5](=[O:38])[N:6]([CH2:11][C:12]2[N:16]([CH3:17])[C:15]([C:18]3[S:26][C:25]4[C:20](=[N:21][CH:22]=[CH:23][C:24]=4[O:27][C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][C:29]=4[F:37])[CH:19]=3)=[N:14][CH:13]=2)[CH2:7][CH2:8][O:9][CH3:10])[CH2:3][CH2:2]1.[Cl-].[NH4+]>CO.[Zn]>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([O:27][C:24]2[CH:23]=[CH:22][N:21]=[C:20]3[CH:19]=[C:18]([C:15]4[N:16]([CH3:17])[C:12]([CH2:11][N:6]([CH2:7][CH2:8][O:9][CH3:10])[C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)=[O:38])=[CH:13][N:14]=4)[S:26][C:25]=23)=[C:29]([F:37])[CH:30]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474402HCID 58474402, compound

Product 1

HCID 58474674HCID 58474674, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 159 (300 mg, 0.555 mmol) in MeOH (10 mL) was added zinc powder (145 mg, 2.22 mmol) and ammonium chloride (59.4 mg, 1.11 mmol) and the reaction mixture was heated to reflux for 3 hours. The mixture was cooled to RT and filtered. The solvent was evaporated and the residue was extracted with DCM. The extract was dried over anhydrous Na2SO4, filtered and concentrated. The crude title compound 160 (283 mg, 100% yield) was used in the next step with no additional purification. MS (m/z)=511.2 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. extractionthe residue was extracted with DCM
  6. dry with materialThe extract was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f51ebc5793d14ae1bcd3b09d2f7e57fe
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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