Ammonium Chloride → HCID 58474785, compound

HRID 1400854Notes

Reaction equation

HRID 1400854 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[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C:22]4=[O:26])[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.[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[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21]5[CH2:25][CH2:24][CH2:23][C:22]5=[O:26])[CH:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474535HCID 58474535, compound

Product 1

HCID 58474785HCID 58474785, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 164 (0.5 g, 1.07 mmol) in MeOH (20 mL) was added Zinc (0.28 g, 4.28 mmol) and ammonium chloride (0.114 g, 2.139 mmol) and the reaction mixture was heated to reflux for 3 hours. The mixture was cooled to RT and filtered. The filtrate was concentrated and the resultant oil was partitioned between water and DCM. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with Et2O to give title compound 165 (0.468 mg, 100% yield, crude) as a black solid. MS (m/z) 438.4 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe resultant oil was partitioned between water and DCM
  6. customThe organic phase was collected
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-19fb56d155ea4646bcf9578fd4ec53ee
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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