Ethanol → HCID 22936907, compound

HRID 387995Notes

Reaction equation

HRID 387995 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.O>C(OCC)(=O)C.CCCCCC.[Fe]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 22936832HCID 22936832, compound

Product 1

HCID 22936907HCID 22936907, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)-4-methylsulfanylphenylamine (620 mg, 1.75 mmol), iron powder (489 mg, 8.75 mmol) and ammonium chloride (936 mg, 17.5 mmol) were suspended in an ethanol (16 ml)-water (4 ml) mixed solvent and the suspension was heated and stirred at 80° C. for 1 hour. Upon completion of the reaction, the reaction mixture was filtered with celite and washed in an ethyl acetate-tetrahydrofuran mixed solvent. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (392 mg, 1.21 mmol, 69%) as colorless crystals.

Workup

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customUpon completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in an ethyl acetate-tetrahydrofuran mixed solvent
  6. washThe organic layer was washed with water and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. filtrationthe crystals were filtered out
  12. washwashed with hexane
  13. customblow-dried

Sources & evidence

ORD record
ord-ddf640944f954ca88795feca9c7ef25e
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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