Hydrochloric Acid → HCID 66750915, compound

HRID 534833Notes

Reaction equation

HRID 534833 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.Cl>COCCOCCOC.C(OCC)(=O)C>[ClH:12].[ClH:14].[C:1]([C:5]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=1[N:7]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 517510HCID 517510, compoundHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 66750915HCID 66750915, compoundYield 14.7%

Reagents, catalysts & solvents 2

HCID 8150DiglymeSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
170 °C

Procedure

A mixture of 2-tert-butyl-4-chloroaniline (Reference Example 19, 16.7 g, 90.8 mmol) and bis(2-chloroethyl)amine hydrochloride (17.8 g, 99.9 mmol) in diglyme (170 mL) was stirred at 170° C. for 3 days under nitrogen atmosphere. After this time, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 1 M NaOH. The organic layer was washed with water, and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting brown oil was purified by flash column chromatography (NH-silica gel, 1:1-0:100 hexane/ethyl acetate, 10:1 ethyl acetate/MeOH) to provide an impure brown oil and a brown solid. The solid was dissolved in ethyl acetate and the solution was treated with 4 M HCl in ethyl acetate to give the title compound (2.17 g) as a brown solid. The impure brown oil was partitioned between ethyl acetate and 1 M HCl and the resulting white precipitate was collected by filtration, and washed with diethyl ether to give the title compound (2.98 g) as a white solid.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and 1 M NaOH
  3. washThe organic layer was washed with water, and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting brown oil was purified by flash column chromatography (NH-silica gel, 1:1-0:100 hexane/ethyl acetate, 10:1 ethyl acetate/MeOH)
  8. customto provide an impure brown oil

Sources & evidence

ORD record
ord-23d3bd23071442aba80a20c0dece0b51
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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