Chlorosuccinimide → HCID 17897329, compound

HRID 2227185Notes

Reaction equation

HRID 2227185 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[Cl:13][C:7]1[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[F:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 27370282,3-Difluoro-6-nitroaniline

Product 1

HCID 17897329HCID 17897329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2,3-Difluoro-6-nitroaniline (15.4 g, 88.7 mmol), N-chlorosuccinimide (14.9 g, 111.4 mmol) and N,N-dimethylformamide (250 mL) were combined and were heated to 80-90° C. for several hours, after which time the mixture was poured into ice water. The product was extracted with ethyl acetate which was then washed with water, saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and the solvents were removed in vacuo to leave a yellow, viscous oil. 1H NMR (DMSO-d6) δ: 8.03 (dd, J=7.3, 2.2 Hz, 1H, Ar—H), 7.65 (br s, 2H, NH2).

Workup

  1. extractionThe product was extracted with ethyl acetate which
  2. washwas then washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customto leave a yellow, viscous oil

Sources & evidence

ORD record
ord-482413f54be44b608a4a9dfcb7b81063
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

Loading…