Methacrylamide → HCID 86682786, compound

HRID 2276692Notes

Reaction equation

HRID 2276692 reaction equation
[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C([N-]C(C)C)(C)C.[Li+].[C:15]12([C:25](Cl)=[O:26])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.C([O:32]C)(C)(C)C>O1CCCC1>[C:1]([NH2:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:15]12([C:25]([OH:26])=[O:32])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

Participants

6

Reactant 4

HCID 6595MethacrylamideHCID 15413tert-Butyl methyl etherHCID 989151-Adamantanecarbonyl chlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 86682786HCID 86682786, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

90.0 g of methacrylamide was dissolved in 1,350 g of tetrahydrofuran (THF), and 944 mL of a 1.12 mol/L lithium diisopropylamide (LiDA) solution was dropwise added thereto at 5° C., followed by stirring for 10 minutes. Subsequently, 900 g of THF having 231.1 g of 1-adamantanecarbonyl chloride dissolved therein was added thereto, followed by stirring at 5° C. for 18 hours. After completion of the reaction, THF and t-butylmethylether (TBME) were added thereto, followed by washing with a 1 wt % aqueous hydrochloric acid solution and pure water, and concentration under reduced pressure. n-hexane was added to the obtained solution, and crystallization was conducted at 5° C., followed by filtration. The obtained solid was dried under reduced pressure, thereby obtaining 194.4 g of 1-adamantanecarboxylic acid methacrylamide (compound (51)).

Workup

  1. customat 5° C.
  2. additiontherein was added
  3. stirringby stirring at 5° C. for 18 hours
  4. additionwere added
  5. washby washing with a 1 wt % aqueous hydrochloric acid solution and pure water, and concentration under reduced pressure
  6. additionn-hexane was added to the obtained solution, and crystallization
  7. customwas conducted at 5° C.
  8. filtrationfollowed by filtration
  9. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-08d319164fbf4e45849736897766035e
Source dataset
uspto-grants-2015_09
Patent number
US09133102B2

Reaction notes

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