Dimethylformamide → HCID 13113821, compound

HRID 1057290Notes

Reaction equation

HRID 1057290 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.CN(C)C=O.[CH2:15]([Li])CCC.[CH3:20][CH2:21][CH2:22][CH2:23][CH2:24]C>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:15])[CH:7]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 178418339Butyllithium

Product 1

HCID 13113821HCID 13113821, compound

Conditions

Temperature
0 °C

Procedure

26 g 4-bromo-N-methylaniline (XXI) and 100 ml anhydrous N,N-dimethyl formamide (HCONEt2) were plced into a four-necked flask and cooled down to 0° C. under nitrogen. 40 ml of 2.5 M n-butyl lithium (n-BuLi) solution in n-hexane was dropped with stirring and stirred for 2 hours while maintaining at 0° C. N-hexane and n-butane were evaporated and 16.2 g bromo-cyclohexane was added and stirred under reflux for 8 hours. After cooling, lithium bromide was filtered off and N,N-dimethyl formamide recovered. The residue was recrystallized twice from 95% ethanol to yield 16 g 4bromo-N-methyl-N-cyclohexyl aniline (II).

Workup

  1. stirringstirred for 2 hours
  2. temperaturewhile maintaining at 0° C
  3. customN-hexane and n-butane were evaporated
  4. addition16.2 g bromo-cyclohexane was added
  5. stirringstirred
  6. temperatureunder reflux for 8 hours
  7. temperatureAfter cooling
  8. filtrationlithium bromide was filtered off
  9. customN,N-dimethyl formamide recovered
  10. customThe residue was recrystallized twice from 95% ethanol

Sources & evidence

ORD record
ord-d72330fc40e74c4e96d6b1c819f7225b
Source dataset
uspto-grants-2003_02
Patent number
US06514956B1

Reaction notes

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