Dichloromethane → 2-(2-Aminoethoxy)-1,3,5-trichlorobenzene

HRID 329770Notes

Reaction equation

HRID 329770 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH2:11][CH2:12][NH:13]CCC.C(Cl)Cl.C(N(CC)CC)C.BrCC(Br)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 3842173N-(2-(2,4,6-Trichlorophenoxy)ethyl)-1-propanamine

Product 1

HCID 71393212-(2-Aminoethoxy)-1,3,5-trichlorobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

N-(n-propyl) ethanolamine 2,4,6-trichlorophenylether, 11.3 gm, was added to 100 ml of methylene chloride. 5.6 ml of triethylamine was added to the system. The system was stirred at about -70° C for 5 minutes and then 3.5 ml of α-bromoacetyl bromide was added dropwise. The system was stirred at room temperature for an additional 18 hours. The reaction was stopped and the system poured into 100 ml of water. The product was extracted with methylene chloride. The organic solution was dried over magnesium sulfate and the methylene chloride was then removed by stripping to give the N-(α-bromoacetyl), N-(npropyl) ethanolamine 2,4,6-trichlorophenylether as a brown oil. Listed as Compound No. 3 in Table I.

Workup

  1. stirringThe system was stirred at room temperature for an additional 18 hours
  2. extractionThe product was extracted with methylene chloride
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. customthe methylene chloride was then removed

Sources & evidence

ORD record
ord-5caa79e9974244b2af0015179e757dba
Source dataset
uspto-grants-1990_01
Patent number
US04892952

Reaction notes

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