Potassium Carbonate → HCID 23326338, compound

HRID 1904045Notes

Reaction equation

HRID 1904045 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[C:21]([F:24])([F:23])[F:22].[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[C:21]([F:22])([F:23])[F:24])[C:8]#[CH:9]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 239041PropargylamineHCID 253877Potassium Bromide

Product 1

HCID 23326338HCID 23326338, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of potassium carbonate (20.0 g) in DMSO (7 ml) was added triethylamine (3 ml) and 2-propyn-1-amine(7.92 g, 1.44×10-1 mole). The reaction mixture was cooled in an ice bath while 1-fluoro-4-nitro-2-trifluoromethylbenzene (30.13 g, 1.44×10-1 mole) was added gradually with stirring. The mixture was gradually allowed to warm to room temperature and stirred for 24 hours. The reaction mixture was poured into excess water and extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on a silica column, eluting with benzene, and recrystallized from benzene to afford yellow crystals; m.p. 71°-72° C. Yield: 24.24 g (69%). I.R. (KBr): 3450 (NH), 3290 (CH), 1588 (Ar-NO2) and 1300 cm-1 (CF3).

Workup

  1. additionwas added gradually
  2. stirringstirred for 24 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on a silica column
  8. washeluting with benzene
  9. customrecrystallized from benzene
  10. customto afford yellow crystals

Sources & evidence

ORD record
ord-559785bf745945cdb518a9368280dc05
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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