Dibromomethane → HCID 86657576, compound

HRID 1471861Notes

Reaction equation

HRID 1471861 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:22](=[S:24])=S.BrCBr.O.[NH2:29][NH2:30]>CC(C)=O.C(O)C>[C:1]1([C:7]2[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:22](=[S:24])[NH:30][N:29]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 99482-PhenylacetophenoneHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 86657576HCID 86657576, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,2-diphenylethanone (10 g, 51.0 mmol) in acetone (250 mL) were added K2CO3 (21.1 g, 153 mmol), CS2 (11.62 g, 153 mmol), and dibromomethane (26.5 g, 153 mmol) at room temperature. The reaction was stirred for 48 h at 40° C. The reaction mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated under reduced pressure. The resulting residue was diluted with ethanol (125 mL) and hydrazine hydrate (2.55 g, 50.9 mmol) was added at room temperature. The reaction was refluxed for 4 h, cooled, and concentrated under reduced pressure. The residue was triturated with isopropanol and dried under reduced pressure to give the title compound as a white solid (8.25 g). LCMS m/z=253.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.14 (bs, 1H), 7.34-7.54 (m, 10H), 12.5 (s, 1H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. additionwas added at room temperature
  5. temperatureThe reaction was refluxed for 4 h
  6. temperaturecooled
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with isopropanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-2c678486f86e43ee99ba5c6e2b84c283
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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