Water → 2,2-Dichloro-N-[(2-ethoxyethoxy)methyl]-N-(3-methylbutyl)acetamide

HRID 364698Notes

Reaction equation

HRID 364698 reaction equation
[CH2:1]([N:6]([CH2:12]Cl)[C:7](=[O:11])[CH:8]([Cl:10])[Cl:9])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH2:14]([O:16][CH2:17][CH2:18][OH:19])[CH3:15].C(N(CC)CC)C.O>C1C=CC=CC=1>[CH2:1]([N:6]([CH2:12][O:19][CH2:18][CH2:17][O:16][CH2:14][CH3:15])[C:7](=[O:11])[CH:8]([Cl:10])[Cl:9])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8076Glycol monoethyl etherHCID 8471TriethylamineHCID 200358492,2-Dichloro-N-(chloromethyl)-N-(3-methylbutyl)acetamide

Product 1

HCID 138242942,2-Dichloro-N-[(2-ethoxyethoxy)methyl]-N-(3-methylbutyl)acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The solution of N-isopentyl-N-chloromethyldichloroacetamide (24.7 g., 0.1 mole) and 2-ethoxyethanol (9.9 g., 10.7 ml., 0.11 mole) in dry benzene (70 ml) is weighed in a four-necked, round-bottom flask of 250 ml, equipped with a calcium chloride tube, reflux condenser, mechanical stirrer, dropping funnel and thermometer. Triethylamine (10.1 g., 13.9 ml., 0.1 mole) is added to this solution under stirring and cooling by water in such a rate that the temperature is maintained below 40° C. After the addition is complete, the mixture is stirred for an additional 2 hours at room temperature. The mixture is washed with water (2×100 ml.) to remove triethylamine hydrochloride and the possible hydrophilic side-product, the benzene solution is dried over anhydrous sodium sulfate after distillation of the solvent and the residue is evaporated to dry under reduced pressure to give 27.9 g. (93%) of the named product as a pale yellow oil which is of 96% purity according to analysis by gas chromatography and is directly useful for practical purposes without any purification; nD25 =1.4649.

Workup

  1. customequipped with a calcium chloride tube
  2. temperaturereflux condenser, mechanical stirrer
  3. temperatureis maintained below 40° C
  4. additionAfter the addition
  5. stirringthe mixture is stirred for an additional 2 hours at room temperature
  6. washThe mixture is washed with water (2×100 ml.)
  7. customto remove triethylamine hydrochloride
  8. dry with materialthe possible hydrophilic side-product, the benzene solution is dried over anhydrous sodium sulfate
  9. distillationafter distillation of the solvent
  10. customthe residue is evaporated
  11. customto dry under reduced pressure
  12. customto give 27.9 g
  13. customis directly useful for practical purposes without any purification

Sources & evidence

ORD record
ord-daf1d51a7f0a48d0b995e860bc895d03
Source dataset
uspto-grants-1986_08
Patent number
US04605764

Reaction notes

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