Ammonium Chloride → HCID 58474708, compound

HRID 1400822Notes

Reaction equation

HRID 1400822 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[N:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C:22]4=[O:26])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CO.O.[Fe]>[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[N:19]=[CH:18][C:17]([CH2:20][N:21]5[CH2:25][CH2:24][CH2:23][C:22]5=[O:26])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474408HCID 58474408, compound

Product 1

HCID 58474708HCID 58474708, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 103 (270 mg, 0.581 mmol), iron (649 mg, 11.63 mmol), and ammonium chloride (187 mg, 3.49 mmol) in MeOH (10 mL) and water (1 mL), was heated to reflux for 3 h, then cooled to RT. The mixture was then filtered through celite and the cake was rinsed with methanol. The mother liquor was concentrated, and partitioned between a saturated aqueous solution of NaHCO3 and ethyl acetate. The aqueous phase was extracted 3 times with DCM. The combined organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, re-dissolved in ethyl acetate, washed with 1N NaOH, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV), to afford the title compound 104 (220 mg, 0.50 mmol, 87% yield) as beige solid. MS (m/z): 435.5 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. filtrationThe mixture was then filtered through celite
  4. washthe cake was rinsed with methanol
  5. concentrationThe mother liquor was concentrated
  6. custompartitioned between a saturated aqueous solution of NaHCO3 and ethyl acetate
  7. extractionThe aqueous phase was extracted 3 times with DCM
  8. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. dissolutionre-dissolved in ethyl acetate
  12. washwashed with 1N NaOH
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe crude product was purified by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV)

Sources & evidence

ORD record
ord-2e65ca2dbdad46e3b04605ae98bc9254
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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