Cyanuric chloride → 1,3-Dichloro-2-(1-chloroethyl)benzene

HRID 1929337Notes

Reaction equation

HRID 1929337 reaction equation
[Cl:1]C1N=C(Cl)N=C(Cl)N=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[CH:18](O)[CH3:19]>CN(C)C=O.ClCCl>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[CH:18]([Cl:1])[CH3:19]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 1037311-(2,6-Dichlorophenyl)ethanol

Product 1

HCID 685154071,3-Dichloro-2-(1-chloroethyl)benzeneYield 100.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

a solution of 5 g of 2,4,6-trichloro-1,3,5-triazine in 5.5 cm3 of N,N-dimethylformamide is stirred for about 3 hours at a temperature close to 20° C. A white precipitate forms. A solution of 5 g of 1-(2,6-dichlorophenyl)-ethanol in 72 cm3 of dichloromethane is added dropwise without exceeding 25° C. After about 48 hours at a temperature close to 20° C., the suspension is solubilized by adding 150 cm3 of dichloromethane. The solution obtained is washed five times with 40 cm3 of water, then dried over magnesium sulphate, filtered and concentrated under reduced pressure. After filtration of the residue on 100 cm3 of silica [eluent: cyclohexane/ethyl acetate (75/25 by volume)], we obtain 5.5 g of 1,3-dichloro-2-(1-chloroethyl)benzene in the form of a colorless oil, which has the following characteristics:

Workup

  1. customclose to 20° C
  2. customwithout exceeding 25° C
  3. customAfter about 48 hours at a temperature close to 20° C.
  4. customThe solution obtained
  5. washis washed five times with 40 cm3 of water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationAfter filtration of the residue on 100 cm3 of silica [eluent: cyclohexane/ethyl acetate (75/25 by volume)], we

Sources & evidence

ORD record
ord-6aa6556f57e34b3a8138b92515ff705c
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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