Dimethylformamide → HCID 22061834, compound

HRID 431399Notes

Reaction equation

HRID 431399 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([S-:12])#[N:11].[K+].CN(C=O)C>C1(C)C=CC=CC=1.O>[S:12]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:10]#[N:11]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 966574-IodobenzaldehydeHCID 516872Potassium thiocyanate

Product 1

HCID 22061834HCID 22061834, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Under an argon atmosphere, a mixture of 4-iodobenzaldehyde (232 mg, 1.00 mmol), KSCN (95.0 mg, 1.00 mmol), CuSCN (120 mg, 1.00 mmol) and DMF (7.5 mL) was heated with stirring in an oil bath maintained at 140° C. for 12 h. After cooling, the mixture was diluted with toluene and water, and then filtered through a Celite bed. The aqueous phase was extracted with toluene, the organic fractions were combined and washed with water, dried and concentrated. The resulting dark oil was chromatographed on silica gel using centrifugal preparative chromatography to obtain off-white crystals (33 mg, 20%). mp 82-83° C.; 1H NMR (CDCl3) δ7.63, 7.92 (AA′BB′, 2H, ArH), 10.01 (s, 1H, CHO); 13C NMR (CDCl3) δ109.4, 129.3, 131.6, 132.9, 191.3; EI-MS obsd 163.0092, calcd exact mass 163.0092 (C8H5NOS); Anal. Calcd. for C8H5NOS: C, 58.88; H, 3.09; N, 8.58; S, 19.65; Found: C, 58.85; H, 2.99; N, 8.61; S, 19.68.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationfiltered through a Celite bed
  4. extractionThe aqueous phase was extracted with toluene
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting dark oil was chromatographed on silica gel using centrifugal preparative chromatography

Sources & evidence

ORD record
ord-3609fb8b2aa04cd887c880dfb6b09e2a
Source dataset
uspto-grants-2003_12
Patent number
US06657884B2

Reaction notes

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