Triethylamine → HCID 68686922, compound

HRID 1441347Notes

Reaction equation

HRID 1441347 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[N:6][O:7][C:8]=1[CH3:9])[CH3:2].C(N(CC)CC)C.[CH3:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>C(Cl)Cl>[C:20]([N:3]([C:4]1[CH:5]=[N:6][O:7][C:8]=1[CH3:9])[CH2:1][CH3:2])(=[O:21])[CH2:19][CH2:18][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 55287999HCID 55287999, compound

Product 1

HCID 68686922HCID 68686922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, ice cooled solution of 4-ethylamino-5-methylisoxazole (Method 5 of WO 03/76436; 49.6 g, 305 mM) and triethylamine (77.0 g, 763 mM, 107 ml) in DCM (800 ml), was slowly added a solution of n-butyryl chloride (35.5, 333 mM, 35 ml) in DCM (100 ml). There was a moderate exotherm. The solution was allowed to warm to ambient temperature and stir for 1 hour. The reaction mixture was washed with water, 2N HCl, brine, sat. NaHCO3 and brine. It was dried and the solvent was evaporated to give the title compound as an oil, which crystallized to a waxy solid (45.1 g, 75%). NMR (300 Mz, DMS0-d6): 0.78 (t, 3H), 0.96 (t, 3H), 1.44 (sext, 2H), 1.93 (t, 2H), 2.33 (s, 3H), 3.49 (q, 2H), 8.68 (s, 1H); m/z 197.

Workup

  1. washThe reaction mixture was washed with water, 2N HCl, brine, sat. NaHCO3 and brine
  2. customIt was dried
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c4b4fc22a87e4b97830db1fad4988742
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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