Dimethylformamide → HCID 22061834, compound

HRID 2111446Notes

Reaction equation

HRID 2111446 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) δ 7.63, 7.92 (AA′BB′, 2H, ArH), 10.01 (s, 1H, CHO); 13C NMR (CDCl3) δ 109.4, 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-44bd6f549a3c4138a71de47e4b6207dd
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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