Hydrochloric Acid → Florox reagent

HRID 1632247Notes

Reaction equation

HRID 1632247 reaction equation
[F:1][C:2]1[C:7]([CH2:8][O:9][N:10]2C(=O)C3=CC=CC=C3C2=O)=[C:6]([F:21])[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24].C(N)CCC.[ClH:30].Cl.NO>C(O)C>[ClH:30].[F:1][C:2]1[C:7]([CH2:8][O:9][NH2:10])=[C:6]([F:21])[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 443297Hydroxyamine hydrochlorideHCID 136577462-[(Perfluorophenyl)methoxy]isoindoline-1,3-dione

Product 1

HCID 122307Florox reagent

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

N-(Pentafluorobenzyloxy)phthalimide 15.9 g, 46 mmol), n-butylamine (3.7 g, 50 mmol) and absolute ethanol (90 ml) were placed in a dry flask under a nitrogen atmosphere. This reaction mixture was stirred at 60° C. for 1 hour, cooled and adjusted to pH 3 using dry hydrogen chloride gas. The resulting white precipitate was filtered and the crystals washed with ice-cold ethanol/ether (1:1). The filtrate was concentrated to give a second crop of crystals. The combined yield of the hydroxylamine hydrochloride was 11.15 g, 99%, m.p. (sublimed) 150°. Analysis: (Found: C, 33.7; H. 2.2; Cl, 13.9; F, 37.8; N, 5.7, C7H5ClF5NO requires C, 33.7; H, 2.0; Cl, 14.2; F, 38.1; N, 5.6%).

Workup

  1. temperaturecooled
  2. filtrationThe resulting white precipitate was filtered
  3. washthe crystals washed with ice-cold ethanol/ether (1:1)
  4. concentrationThe filtrate was concentrated
  5. customto give a second crop of crystals
  6. custom11.15 g, 99%, m.p. (sublimed) 150°

Sources & evidence

ORD record
ord-1a20c31e2e734db590fd7515e7b6bb78
Source dataset
uspto-grants-1984_10
Patent number
US04474815

Reaction notes

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