Epichlorohydrin → HCID 20458578, compound

HRID 544735Notes

Reaction equation

HRID 544735 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>C(O)(=O)C>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[N:6]([CH2:16][CH:18]1[O:20][CH2:19]1)[CH2:16][CH:18]1[O:20][CH2:19]1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-

Product 1

HCID 20458578HCID 20458578, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,5-bis(trifluoromethyl)aniline (22.9 g) and epichlorohydrin (37 g) in glacial acetic acid (10.6 g) were heated at about 100° C. for about 11 hours. Excess epichlorohydrin was distilled off under reduced pressure. Benzene (100 cm3), a solution of sodium hydroxide (8 g) in water (30 cm3) and benzyltriethylammonium chloride (0.3 g) was added to the residue and the mixture stirred at about room temperature for about 15 minutes, followed by 15 minutes at about 60° C. The aqueous layer was discarded. The dehydrochlorination procedure was repeated three times in order to effect complete conversion. The solvent was removed and the product was purified by preparative high performance liquid chromatography to give 19.5 g of 3,5-bis(trifluoromethyl)-N,N-bis(2,3-epoxypropyl)aniline.

Workup

  1. distillationExcess epichlorohydrin was distilled off under reduced pressure
  2. additionBenzene (100 cm3), a solution of sodium hydroxide (8 g) in water (30 cm3) and benzyltriethylammonium chloride (0.3 g) was added to the residue
  3. waitfollowed by 15 minutes at about 60° C
  4. customThe solvent was removed
  5. customthe product was purified by preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-c2b2a2662c94497c9a6bcd2abb745e1c
Source dataset
uspto-grants-1984_05
Patent number
US04451645

Reaction notes

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