Water → HCID 66808527, compound

HRID 607319Notes

Reaction equation

HRID 607319 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.[Cl-].[NH4+].O1CCCC1.O>CO.[Fe]>[NH2:16][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 610314684-(4-Bromo-2-nitro-phenylsulfanyl)-phenol

Product 1

HCID 66808527HCID 66808527, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from Example 238A (0.302 g, 0.926 mmol), iron powder (0.208 g, 3.7 mmol, 4.0 eq) and ammonium chloride (0.059 g, 1.11 mmol, 1.2 eq) in a mixture of methanol (6 mL), tetrahydrofuran (6 mL), and water (2 mL) was heated under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered through Celite and the filter pad was rinsed with methanol (25 mL). The filtrate was evaporated under reduced pressure to leave a brown glassy solid (0.27 g, 99%) that was utilized without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filter pad was rinsed with methanol (25 mL)
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-155cfaa2dd0145b6acad01c68b536902
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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