Hydrochloric Acid → HCID 11701588, compound

HRID 1826238Notes

Reaction equation

HRID 1826238 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Br[CH2:11][CH2:12][CH2:13][Cl:14].C(N(CC)CC)C.Cl>C(C(C)=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH:5][CH2:11][CH2:12][CH2:13][Cl:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72553-Chloro-4-methylanilineHCID 80061-Bromo-3-chloropropaneHCID 8471Triethylamine

Product 1

HCID 11701588HCID 11701588, compoundYield 157.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-Chloro-4-methylaniline (10.0 g, 70.6 mmol), 1-bromo-3-chloropropane (34.7 mL, 55.6 g, 353 mmol) and triethylamine (21.4 g, 212 mmol) were charged. The mixture was stirred at 25–28° C. for 24 hrs. Water (50 mL) and methyl ethyl ketone (25 mL) were added for partitioning. The organic layer was washed twice with water (50 mL). Conc. hydrochloric acid (35 mL, 5.7 eq) was dropwise added to the organic layer under ice-cooling. The mixture was stirred at room temperature for 1 hr. The crystals were collected by filtration, washed with diisopropyl ether (10 mL) and dried in vacuo at 50° C. to give the title compound (14.12 g, yield 78.5%) as pale-yellow crystals.

Workup

  1. customfor partitioning
  2. washThe organic layer was washed twice with water (50 mL)
  3. temperaturecooling
  4. stirringThe mixture was stirred at room temperature for 1 hr
  5. filtrationThe crystals were collected by filtration
  6. washwashed with diisopropyl ether (10 mL)
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-b568c30cb4d34cacb16ce9ef413e42d3
Source dataset
uspto-grants-2006_05
Patent number
US07049441B2

Reaction notes

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