2-Bromo-1-(3-nitrophenyl)ethan-1-one → HCID 68285207, compound

HRID 1497664Notes

Reaction equation

HRID 1497664 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[O:14]1[CH2:19][CH2:18][CH:17]([C:20](=[S:22])[NH2:21])[CH2:16][CH2:15]1>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[N:21]=[C:20]([CH:17]3[CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)[S:22][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 13197204Oxane-4-carbothioamide

Product 1

HCID 68285207HCID 68285207, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(3-nitrophenyl)ethanone (245 mg, 1 mmol) and tetrahydro-2H-pyran-4-carbothioamide (144 mg, 1 mmol) is suspended in absolute ethanol (20 mL) and heated to reflux for 2 h. The solution is then cooled and evaporated to dryness. The crude is dissolved in DCM and washed twice with a solution of saturated sodium bicarbonate and once with water. The organic layer is dried up with sodium sulfate, filtered and evaporated to dryness to yield 285 mg of the title compound (98%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe solution is then cooled
  4. customevaporated to dryness
  5. dissolutionThe crude is dissolved in DCM
  6. washwashed twice with a solution of saturated sodium bicarbonate and once with water
  7. dry with materialThe organic layer is dried up with sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-be54e76839fb45238b7bd0e3ed03e1ad
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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