Ammonium Chloride → HCID 58790297, compound

HRID 418626Notes

Reaction equation

HRID 418626 reaction equation
[F:1][C:2]1[CH:33]=[C:32]([N+:34]([O-])=O)[CH:31]=[CH:30][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]=[CH:16][N:17]([CH2:19][CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:34][C:32]1[CH:31]=[CH:30][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]=[CH:16][N:17]([CH2:19][CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:18]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:33]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58790189HCID 58790189, compound

Product 1

HCID 58790297HCID 58790297, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 99 (30 mg, 0.058 mmol) in EtOH (1.6 ml) and water (0.6 ml) was added ammonium chloride (3 mg, 0.9 eq, 0.053 mmol) and Fe (28 mg, 8.5 eq, 0.49 mmol) and the reaction mixture was heated to reflux for 45 min. The reaction mixture was cooled to RT, filtered through celite then concentrated to afford title compound 100 (30 mg, 100% yield). MS (m/z): 484.1 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 45 min
  3. filtrationfiltered through celite
  4. concentrationthen concentrated

Sources & evidence

ORD record
ord-e85f3e720e7b4dd39766557d7715ec47
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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