Potassium Carbonate → HCID 23326340, compound

HRID 1904043Notes

Reaction equation

HRID 1904043 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:10])[C:8]#[CH:9].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21].[K+].[Br-]>CS(C)=O.O.C(N(CC)CC)C>[CH2:7]([NH:10][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21])[C:8]#[CH:9]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 239041PropargylamineHCID 253877Potassium Bromide

Product 1

HCID 23326340HCID 23326340, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of potassium carbonate (20.0 g) in DMSO (7 ml) was added triethylamine (3 ml) and 2-propyn-1-amine (7.10 g, 1.29×10-1 mole). 2-Fluoro-5-nitrotoluene (20.00 g, 1.29×10-1 mole) was added with stirring and the reaction mixture was heated at 50° C. for three days. The mixture was cooled, poured into excess water, and extracted with methylene chloride. The methylene chloride solution was dried over sodium sulfate, filtered and evaporated. The residue was chromotographed on a silica column, eluting with benzene, and recrystallized from benzene to afford yellow crystals; m.p. 121°-123° C. Yield: 15.02 g (61%). I.R. (KBr): 3344 (NH), 3226 (CH), 1580 and 1282 cm-1 (Ar-NO2).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. washeluting with benzene
  7. customrecrystallized from benzene
  8. customto afford yellow crystals

Sources & evidence

ORD record
ord-50c5ae86bdcc4acfbadfb02028d6d6d3
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

Loading…