Ammonium Chloride → HCID 58474350, compound

HRID 1400843Notes

Reaction equation

HRID 1400843 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][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:19]=[CH:18][C:17]([CH2:20][N:21]4[C:25](=[O:26])[CH2:24][CH2:23][C:22]4=[O:27])=[CH:16][CH:15]=3)[S:13][C:6]=12.[NH4+].[Cl-]>CO.O.[Zn]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:19]=[CH:18][C:17]([CH2:20][N:21]5[C:22](=[O:27])[CH2:23][CH2:24][C:25]5=[O:26])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:31]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474503HCID 58474503, compound

Product 1

HCID 58474350HCID 58474350, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 138 (100 mg, 0.209 mmol) in MeOH (10 mL) was added zinc (109 mg, 1.672 mmol) and NH4Cl (44.7 mg, 0.836 mmol) in water (1 mL) and the reaction mixture was heated to reflux for 48 hrs, cooled to RT and concentrated. The crude product was dissolved in MeOH/DCM and washed with water. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated to afford title compound 139 (80 mg, 85% yield) that was used without additional purification. MS (m/z)=448.47 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 48 hrs
  3. concentrationconcentrated
  4. dissolutionThe crude product was dissolved in MeOH/DCM
  5. washwashed with water
  6. customThe organic phase was collected
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0cdfcc20eeb446c4ae8ccba482adf032
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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