Hydrochloric Acid → HCID 5702423, compound

HRID 2377248Notes

Reaction equation

HRID 2377248 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].[OH-].[Na+].Cl>CO.O>[N+:8](/[CH:11]=[CH:6]/[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 5702423HCID 5702423, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-thiophenecarboxaldehyde (57.0 g, 502 mmol) and nitromethane (29.9 mL, 552 mmol) in methanol (100 mL) was added a solution of sodium hydroxide (22.1 g, 552 mmol) in water (45 mL) at a rate that kept the temperature at less than 5° C. The mixture was allowed to stand at about 0° C. for about 30 minutes. The precipitate was collected by filtration, dissolved in a minimum amount of ice-cold water and, poured into an ice-cold mixture of concentrated hydrochloric acid (96.7 mL, 1178 mmol) and water (152 mL). The precipitate was collected by filtration and was recrystallized from aqueous ethanol to provide the desired product. MS (DCI-NH3): m/z 173 (M+NH4)+.

Workup

  1. customat less than 5° C
  2. filtrationThe precipitate was collected by filtration
  3. dissolutiondissolved in a minimum amount of ice-cold water
  4. filtrationThe precipitate was collected by filtration
  5. customwas recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-7121e6db13bc41dfb9b644ac5bfa95c5
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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