Ethyl Acetate → HCID 43156232, compound

HRID 851963Notes

Reaction equation

HRID 851963 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.C(OCC)(=O)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:15][CH:12]2[CH2:14][CH2:13]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 69828CyclopropylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 43156232HCID 43156232, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloromethyl-benzoyl chloride (2.82 g, 15 mmol) and cyclopropylamine (1.26 ml, 18 mmol) were reacted in CH2Cl2 (30 ml) and in the presence of Hünig's base (3.1 ml, 18 mmol) for 1 h. A precipitate was formed which was resolubilzed by adding ethyl acetate. The reaction mixture was washed with a 5% KHSO4/10% K2SO4 solution, NaCl sat. solution and dried (Na2SO4). The organic phase was filtered and concentrated under reduced pressure to yield a semi-solid which was triturated in hexanes: solid 3.1 g (95%); 1H NMR (CDCl3) δ 0.60-0.64 (m, 2H), 0.85-0.90 (m, 2H), 2.89-2.92 (m, 1H), 4.60 (s, 2H), 6.20 (br, 1H), 7.44 (d, 2H), 7.71-7.74 (m, 2H); MS: m/e=210.2 (MH+)

Workup

  1. customA precipitate was formed which
  2. washThe reaction mixture was washed with a 5% KHSO4/10% K2SO4 solution, NaCl sat. solution
  3. dry with materialdried (Na2SO4)
  4. filtrationThe organic phase was filtered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a semi-solid which
  7. customwas triturated in hexanes

Sources & evidence

ORD record
ord-3ee276e38e354d6bbf4128a65f871c28
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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