Hydrochloric Acid → HCID 61438572, compound

HRID 602510Notes

Reaction equation

HRID 602510 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:19])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=2)=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Fe]>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]([CH3:19])[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:18])[CH:10]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 67267225HCID 67267225, compound

Product 1

HCID 61438572HCID 61438572, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (5-chloro-thiophen-2-ylmethyl)-(methyl)-(3-methyl-4-nitrophenyl)-amine (1.85 g, 6.23 mmol) and iron powder (2.09 g, 37.4 mmol) in ethanol (60 mL) was added 6 N HCl (12.5 mL, 75 mmol), and the mixture was stirred vigorously at +60° C. for 50 minutes. It was then poured into saturated aqueous sodium bicarbonate (200 mL) to which enough sodium carbonate was added to attain a pH>10. The resulting mixture was extracted with ethyl acetate (200 mL, then 2×100 mL), the extract was dried over sodium sulfate and volatiles were evaporated. The residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield the title compound as a brown oil (1.51 g, 91%).

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with ethyl acetate (200 mL
  3. dry with material2×100 mL), the extract was dried over sodium sulfate and volatiles
  4. customwere evaporated
  5. customThe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-9c0e132653e441478359f3905b7a2cd7
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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