Nitromethane → HCID 68970262, compound

HRID 1891942Notes

Reaction equation

HRID 1891942 reaction equation
[CH2:1]([S:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH3:20])([O-:19])=[O:18].[C:21]([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:15][C:16]=1/[CH:21]=[CH:20]/[N+:17]([O-:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 128424604-(Benzylsulfanyl)benzaldehyde

Product 1

HCID 68970262HCID 68970262, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-benzylsulfanyl-benzaldehyde (840 mg 3.68 mmol) described in Manufacturing Example 205-1-2, nitromethane (997 μL, 18.4 mmol), ammonium acetate (567 mg, 7.36 mmol), and acetic acid (10 mL) was stirred for 2 hours at 100° C. This mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (950 mg). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned into ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-71ade09374a2495aa3251892629ac61c
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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