Ammonium Chloride → HCID 17859515, compound

HRID 1372608Notes

Reaction equation

HRID 1372608 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][S:8][C:9]2[CH:10]=[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=2[N+:15]([O-])=O)=[CH:5][CH:4]=1.[Cl-].[NH4+]>C(O)C.C1COCC1.O>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][S:8][C:9]2[CH:10]=[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=2[NH2:15])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 17858869HCID 17858869, compound

Product 1

HCID 17859515HCID 17859515, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

Under stirring, a solution of ethyl 3-(4-methoxybenzylthio)-4-nitrophenylacetate (3.33 g, 9.92 mmol), ammonium chloride (542 mg, 10.1 mmol) and reduced iron powder (2.57 g, 46.1 mmol) in ethanol/THF/water (2:2:1, 75 ml) was heated and refluxed for 1.5 hours. After the reaction mixture was cooled, the insoluble matter was filtered off. The filtrate was distilled under reduced pressure to remove the solvent. The residue was neutralized by pouring therein a saturated aqueous solution of sodium bicarbonate, followed by extraction with a chloroform-methanol mixture. The extract was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (20:1) eluate fractions, ethyl 3-(4-methoxybenzylthio)-4-aminophenylacetate (2.64 g, 86%) was obtained as a yellow oil.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. filtrationthe insoluble matter was filtered off
  4. distillationThe filtrate was distilled under reduced pressure
  5. customto remove the solvent
  6. additionby pouring
  7. extractiona saturated aqueous solution of sodium bicarbonate, followed by extraction with a chloroform-methanol mixture
  8. dry with materialThe extract was dried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (20:1) eluate fractions

Sources & evidence

ORD record
ord-76d1fbe1717a452fb3969eebc3cea1e7
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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