Hydrochloric Acid → HCID 54292766, compound

HRID 365532Notes

Reaction equation

HRID 365532 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:13][C:14]([CH3:19])=[CH:15][C:16](Cl)=[O:17].N1C=CC=CC=1.Cl>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH:10]([CH3:12])[CH3:11])[C:16](=[O:17])[CH:15]=[C:14]([CH3:19])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1023943-Methyl-2-butenoyl chlorideHCID 23291925298185-50-92×

Product 1

HCID 54292766HCID 54292766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(3-Bromo-4-methyl-phenyl)-isopropyl-amine (Compound 41, 36.78 g, 161.2 mmol) was dissolved in dichloromethane (200 mL) and the solution was cooled to 0° C. and treated with 3,3-dimethylacryloyl chloride (28.6 g, 241.8 mmol) and then pyridine (36 mL). The solution was stirred at 0° C. for 1 hour and at room temperature for 5 hours. The mixture was poured into separatory funnel containing dichloromethane and 10% aqueous HCl. The layers were separated and the aqueous layer extracted twice with dichloromethane. The combined organic layers were washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure to give the title compound, which was used directly for the next reaction without further purification, as a solid: Rf=0.48, 20% ethyl acetate in hexane:

Workup

  1. additionThe mixture was poured into separatory funnel
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted twice with dichloromethane
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb6d264697cd41c6963104fe661b417e
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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