Water → HCID 22921579, compound

HRID 2258610Notes

Reaction equation

HRID 2258610 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[CH2:19]([NH2:22])[C:20]#[CH:21].O>O1CCOCC1>[CH2:19]([NH:22][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[C:20]#[CH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 677672,5-DifluoronitrobenzeneHCID 239041Propargylamine

Product 1

HCID 22921579HCID 22921579, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 15.0 grams (0.094 mole) of 2,5-difluoronitrobenzene in 250 mL of dioxane was added 100 mL of triethylamine, followed by 7.3 grams (0.132 mole) of 2-propyn-1-ylamine. The reaction mixture was then warmed to reflux, where it was stirred for about four hours, then cooled to ambient temperature and poured into cold water. The resultant solid precipitate was collected by filtration and dried, yielding 10.0 grams of N-(2-propyn-1-yl)-4-fluoro-2-nitroaniline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was then warmed
  2. temperatureto reflux
  3. filtrationThe resultant solid precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-c2c7baf4d98042d4bdb232f86b5f1d9d
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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