Ammonium Chloride → HCID 66808364, compound

HRID 607310Notes

Reaction equation

HRID 607310 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[C:9]([N+:21]([O-])=O)[CH:8]=1.[Cl-].[NH4+]>O1CCCC1.O.C(O)C.[Fe]>[NH2:21][C:9]1[CH:8]=[C:7]([CH2:6][O:5][C:4]2[CH:24]=[CH:25][CH:26]=[C:2]([Br:1])[CH:3]=2)[CH:12]=[CH:11][C:10]=1[S:13][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 60204830HCID 60204830, compound

Product 1

HCID 66808364HCID 66808364, compoundYield 79.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[4-(3-Bromo-phenoxymethyl)-2-nitro-phenylsulfanyl]-phenol (325 mg, 0.752 mmol), iron dust (210 mg, 3.76 mmol) and ammonium chloride (60 mg, 1.13 mmol) in tetrahydrofuran (5 mL), water (1.5 mL) and ethanol (5 mL) was heated at reflux for 2.5 hours. After cooling to room temperature, the solution was filtered through a pad of celite, which was washed with methanol. The filtrate was then concentrated under vacuum, then dissolved in water (20 mL) and extracted with ethyl acetate (2×20 mL). The organic extracts were dried and concentrated under vacuum to provide the title compound as a light yellow solid (240 mg, 79%).

Workup

  1. temperatureat reflux for 2.5 hours
  2. filtrationthe solution was filtered through a pad of celite, which
  3. washwas washed with methanol
  4. concentrationThe filtrate was then concentrated under vacuum
  5. dissolutiondissolved in water (20 mL)
  6. extractionextracted with ethyl acetate (2×20 mL)
  7. customThe organic extracts were dried
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-432528b5c6154e9b96250f74282c1417
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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