Ammonium Chloride → HCID 58236582, compound

HRID 1026834Notes

Reaction equation

HRID 1026834 reaction equation
[F:1][C:2]1[CH:42]=[C:41]([N+:43]([O-])=O)[CH:40]=[CH:39][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:38]=[CH:37][C:17]([CH2:18][N:19]([CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:43][C:41]1[CH:40]=[CH:39][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:38]=[CH:37][C:17]([CH2:18][N:19]([CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:42]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58236629HCID 58236629, compound

Product 1

HCID 58236582HCID 58236582, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 365 (0.49 g, 0.76 mmol) in MeOH (100 mL) was added iron dust (0.43 g, 7.6 mmol) and ammonium chloride (0.12 g, 2.3 mmol) in water (5 mL). The resulting mixture was heated to reflux for 4 h, then cooled, filtered through a celite pad and concentrated. The residue was partitioned between dichloromethane and water; the organic phase was collected, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (eluent 2% MeOH in EtOAc) to give 366 (0.41 g, 88% yield). LRMS (M+H): 612.6

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. temperaturecooled
  4. filtrationfiltered through a celite pad
  5. concentrationconcentrated
  6. customThe residue was partitioned between dichloromethane and water
  7. customthe organic phase was collected
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel chromatography (eluent 2% MeOH in EtOAc)

Sources & evidence

ORD record
ord-0be7b15571104332842455025880145c
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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