Cyclopropylamine → 4-Bromo-N-cyclopropyl-2-fluoro-N'-hydroxybenzenecarboximidamide

HRID 1988896Notes

Reaction equation

HRID 1988896 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](Cl)=[N:13][OH:14])=[C:8]([F:16])[CH:7]=1>CCOCC>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[N:13][OH:14])[NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:8]([F:16])[CH:7]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 734619254-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chloride2×

Product 1

HCID 1785263504-Bromo-N-cyclopropyl-2-fluoro-N'-hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclopropylamine (1.6 ml) was added dropwise to an ice-old solution of 4-bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chloride (Intermediate 51) (0.59 g) in dry ether (25 ml) under nitrogen. After the addition the mixture was allowed to warm to room temp. then stirred for 18 h. The resulting precipitate was collected by filtration then purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (3:2) to give the title compound as a white solid (0.435 g).

Workup

  1. additionAfter the addition the mixture
  2. temperatureto warm to room temp.
  3. filtrationThe resulting precipitate was collected by filtration
  4. customthen purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (3:2)

Sources & evidence

ORD record
ord-5bc5634ca2d44b7fae0a048be6d06fce
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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