N-bromobutanimide → 2-Bromo-6-chloro-5-dimethylaminoaniline

HRID 352464Notes

Reaction equation

HRID 352464 reaction equation
[Cl:1][C:2]1[C:8]([N:9]([CH3:11])[CH3:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:12]N1C(=O)CCC1=O>CN(C=O)C>[Br:12][C:5]1[CH:6]=[CH:7][C:8]([N:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 227123462-Chloro-3-dimethylaminoaniline

Product 1

HCID 227123472-Bromo-6-chloro-5-dimethylaminoanilineYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

12.8 g of 2-chloro-3-dimethylaminoaniline is dissolved in 180 ml of DMF and stirred at 0° C. A solution of 13.4 g of N-bromosuccinimide in 80 ml of DMF is slowly added dropwise, so that the temperature does not rise above 2° C. The mixture is stirred for 5 hours at 0° C. and then at RT. After 48 hours, 700 ml of ice-water is added. The white precipitate is filtered off and the aqueous phase is extracted three times with 200 ml of diethyl ether. The organic phases are dried, filtered, and evaporated down. 17.5 g of 2-bromo-6-chloro-5-dimethylaminoaniline is obtained as a brown oil and used further without any additional purification.

Workup

  1. customdoes not rise above 2° C
  2. stirringThe mixture is stirred for 5 hours at 0° C.
  3. customat RT
  4. filtrationThe white precipitate is filtered off
  5. extractionthe aqueous phase is extracted three times with 200 ml of diethyl ether
  6. customThe organic phases are dried
  7. filtrationfiltered
  8. customevaporated down

Sources & evidence

ORD record
ord-813c36f13bd94505be7af6937ef220fb
Source dataset
uspto-grants-2004_06
Patent number
US06747051B2

Reaction notes

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