Dimethylformamide → HCID 911944, compound

HRID 1260334Notes

Reaction equation

HRID 1260334 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[C:18]=[S:19].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[O:29]>C(OCC)(=O)C>[NH2:4][C:3]1[C:2]([C:1]#[N:5])=[C:18]([NH:17][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:19][C:27]=1[C:28](=[O:29])[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7673Phenyl IsothiocyanateHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 911944HCID 911944, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Malononitrile (0.661 g, 0.0100 mol) was dissolved in N,N-dimethylformamide (50 mL, 0.6 mol) and was stirred under an atmosphere of Argon. Potassium carbonate (1.52 g, 0.0110 mol) was added and was stirred for 30 minutes. Isothiocyanatobenzene (1.49 g, 0.0110 mol) was added and the reaction mixture was stirred for 2 hours. 2-Bromo-1-(4-methylphenyl)-ethanone, (2.34 g, 0.0110 mol) was added and the reaction mixture was allowed to stir overnight. The resultant dark red solution was diluted with 150 mL ethyl acetate and washed successively with 100 mL each of ½ saturated NaHCO3 solution, IN LiCl (2×) and 1N Na2 S2O3. The combined aqueous layers were discarded and the organic layer was dried, filtered, and evaporated to collect 1.46 g of the desired product as pale yellow-orange crystals. MS (ESI) [M+H+]+=334.2.

Workup

  1. stirringwas stirred for 30 minutes
  2. stirringthe reaction mixture was stirred for 2 hours
  3. stirringto stir overnight
  4. washwashed successively with 100 mL each of ½ saturated NaHCO3 solution, IN LiCl (2×)
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto collect 1.46 g of the desired product as pale yellow-orange crystals

Sources & evidence

ORD record
ord-9cad994c07394ce99dc1cc3c9eeaf577
Source dataset
uspto-grants-2013_06
Patent number
US08470821B2

Reaction notes

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