Hydrochloric Acid → HCID 86722743, compound

HRID 1525797Notes

Reaction equation

HRID 1525797 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Br:30][CH2:31][C:32](Cl)=[O:33].Cl>ClCCl>[Br:30][CH2:31][C:32]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 86722740HCID 86722740, compound

Product 1

HCID 86722743HCID 86722743, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 8 (1.5 g) was dissolved in dichloromethane (10 mL). Potassium carbonate (980 mg) and the solution of bromoacetyl chloride (890 mg) in dichloromethane (5 mL) was added thereto at 0° C., followed by stirring for 1.5 hours. The reaction solution cooled with ice was poured into 1N hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (1.7 g) having the following physical property values.

Workup

  1. customat 0° C.
  2. temperatureThe reaction solution cooled with ice
  3. extractionfollowed by extraction with dichloromethane
  4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f32d60d83dc84045ad86df23ca38e0e3
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

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