2,6-Dimethylaniline → HCID 67215468, compound

HRID 2421444Notes

Reaction equation

HRID 2421444 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][Br:15])#[N:11]>C1(C)C=CC=CC=1>[BrH:15].[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:4]1[CH2:14][C:13]2[C:12](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[NH:11]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 67215468HCID 67215468, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-dimethylaniline (6.2 g, 51 mmol) was added to a solution of 2-cyanobenzylbromide (10.0 g, 51 mmol) in toluene (250 ml). The solution was heated to reflux for 18 hours. The formed solid was filtered off and washed with toluene (2×25 ml). After drying 11.5 g of the desired compound was obtained as a white solid. The filtrate was heated to reflux for 20 hours. Another 1.5 g of pure product was obtained leading to a total yield of 13.0 g (80%). The product was characterized by

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe formed solid was filtered off
  4. washwashed with toluene (2×25 ml)
  5. dry with materialAfter drying 11.5 g of the desired compound
  6. customwas obtained as a white solid
  7. temperatureThe filtrate was heated
  8. temperatureto reflux for 20 hours

Sources & evidence

ORD record
ord-4ae9ac6378914980b88996d9ccbf04ec
Source dataset
uspto-grants-2011_06
Patent number
US07956140B2

Reaction notes

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