Hydrochloric Acid → HCID 11701588, compound
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
Conditions
- Temperature
- 26.5 °C
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
- customfor partitioning
- washThe organic layer was washed twice with water (50 mL)
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 1 hr
- filtrationThe crystals were collected by filtration
- washwashed with diisopropyl ether (10 mL)
- customdried in vacuo at 50° C.
Sources & evidence
- ORD record
- ord-ef704f01042f43d39960a585c7fbaa4e
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833457B1
Reaction notes
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