Potassium Carbonate → HCID 23326339, compound

HRID 1904047Notes

Reaction equation

HRID 1904047 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:10])[C:8]#[CH:9].[F:11][C:12]1[CH:17]=[C:16](F)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].[K+].[Br-]>CC(C)=O.O.C(N(CC)CC)C>[CH2:7]([NH:10][C:16]1[CH:17]=[C:12]([F:11])[C:13]([N+:22]([O-:24])=[O:23])=[CH:14][C:15]=1[N+:19]([O-:21])=[O:20])[C:8]#[CH:9]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 675981,5-Difluoro-2,4-dinitrobenzeneHCID 239041PropargylamineHCID 253877Potassium Bromide

Product 1

HCID 23326339HCID 23326339, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of potassium carbonate (6.0 g) in acetone (25 ml) was added triethylamine (1.5 ml) and 2-propyn-1-amine (2.35 g, 4.25×10-2 mole). 1,5-Difluoro-2,4-dinitrobenzene (10.00 g, 4.90×10-2 mole) was added and the reaction mixture was stirred at room temperature for 24 hours. The mixture was poured into excess water and filtered. The resulting dark solid was chromatographed on a silica column, eluting with benzene, and recrystallized from benzene to afford yellow crystals; m.p. 113°-115° C. Yield: 8.33 g (82%). I.R. (KBr): 3340 (NH), 3280 (CH), 1615, 1260 (Ar-NO2) and 1210 cm-1 (Ar-F).

Workup

  1. filtrationfiltered
  2. customThe resulting dark solid was chromatographed on a silica column
  3. washeluting with benzene
  4. customrecrystallized from benzene
  5. customto afford yellow crystals

Sources & evidence

ORD record
ord-d7c992aecc424a368ba86d9fc4b6adbb
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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