1,2-Dichloroethane → HCID 86681268, compound

HRID 336600Notes

Reaction equation

HRID 336600 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[NH:5][CH3:6].C(N(C(C)C)CC)(C)C.ClCCCl.[C:24]12([C:34](Cl)=[O:35])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([N:5]([CH3:6])[C:34]([C:24]23[CH2:33][CH:28]4[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]4)[CH2:25]2)[CH2:31]3)=[O:35])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 599563303-Bromo-N,2-dimethylbenzenamine

Product 1

HCID 86681268HCID 86681268, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

3-Bromo-N,2-dimethylaniline (300 mg) and diisopropylethylamine (581 mg) were added to 1,2-dichloroethane (5 mL). 1-Adamantanecarbonyl chloride (328 mg) was added and the solution was heated at 50° C. for three days. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1M aqueous HCl, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash column chromatography on silica gel using 10% ethyl acetate (hexanes) to yield the title compound.

Workup

  1. washwashed three times with 1M aqueous HCl
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel using 10% ethyl acetate (hexanes)

Sources & evidence

ORD record
ord-e12becb22a07441c9b6fd452a1327efc
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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