Water → HCID 10448353, compound

HRID 486691Notes

Reaction equation

HRID 486691 reaction equation
Cl.[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH:8]([NH:23][CH3:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-])=O.O>[Fe].C(O)C>[NH2:20][C:11]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=1[CH2:9][CH:8]([C:4]1[S:5][CH:6]=[CH:7][C:3]=1[CH3:2])[NH:23][CH3:24]

Participants

5

Reactant 2

HCID 962WaterHCID 22414508HCID 22414508, compound

Product 1

HCID 10448353HCID 10448353, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.3 g of α-(3-methyl-2-thienyl)-N-methyl-2-nitro-4-trifluoromethylbenzeneethanamine hydrochloride, 4.8 g of iron powder, 13 ml of water, 50 ml of 95% ethanol, and concentrated 350 μl hydrochloric acid was refluxed for 1.5 hrs. The mixture was filtered through Celite, the filter cake washed with water, and the organic phase of the filtrate was concentrated in vacuo. The residue was diluted with 50 ml of water and basified with 10% (aq) sodium hydroxide solution. The aqueous phase was extracted with dichloromethane, and the combined organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was triturated with hexane to afford 2.1 g of product, mp 52°-54° C.

Workup

  1. concentrationconcentrated 350 μl hydrochloric acid
  2. temperaturewas refluxed for 1.5 hrs
  3. filtrationThe mixture was filtered through Celite
  4. washthe filter cake washed with water
  5. concentrationthe organic phase of the filtrate was concentrated in vacuo
  6. additionThe residue was diluted with 50 ml of water
  7. extractionThe aqueous phase was extracted with dichloromethane
  8. dry with materialthe combined organic phase was dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-dc7da99f302244888a0b425083cf3168
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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