Triethylamine → HCID 25102948, compound

HRID 238558Notes

Reaction equation

HRID 238558 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:7].[CH2:8]([N:10](CC)CC)C.[N:15]1[O:16][N:17]=[C:18]2[CH:23]=[C:22]([C:24](Cl)=[O:25])[CH:21]=[CH:20][C:19]=12>CN.C(O)C.ClCCl>[CH3:8][N:10]([CH:4]1[CH2:5][CH2:6][O:1][C:2](=[O:7])[CH2:3]1)[C:24]([C:22]1[CH:21]=[CH:20][C:19]2=[N:15][O:16][N:17]=[C:18]2[CH:23]=1)=[O:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 5206603393-45-1HCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

Product 1

HCID 25102948HCID 25102948, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6329MethylamineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
55 °C

Procedure

5,6-Dihydro-2H-pyran-2-one (1.0 g, 10.2 mmol) was dissolved in 3 ml of a 33% solution of methylamine in ethanol and heated to 55° C. overnight. The solvent was evaporated, the residue dissolved in methanol (20 ml) and conc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h. The mixture was evaporated to dryness, the residue dissolved in THF (20 ml), dichloromethane (20 ml) and triethylamine (3 ml) and a solution of [2,1,3]-benzoxadiazole-5-carboxylic acid chloride (2.0 g, 11 mmol), in dichloromethane (5 ml), added. After stirring the mixture for 0.75 h, the mixture was washed with 1N HCl and conc. NaHCO3 solution, dried over sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column using ethyl acetate/hexane/dichloromethane (70:20:10), to give N-methyl-N-(2-oxotetrahydro-2H-pyran-4-yl)-[2,1,3]-benzoxadiazole-5-carboxamide as white solid after crystallization from dichloromethane/methanol (0.21 g). Mp=169-171° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.97 (d, J=9.0 Hz, 1H); 7.90 (s, 1H); 7.40 (d, J=9.0 Hz, 1H); 5.10-4.40 (m, 3H); 3.01 (s, 3H); 3.00-2.74 (m, 2H) and 2.60-2.10 ppm (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (20 ml)
  3. temperatureconc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue dissolved in THF (20 ml)
  6. washthe mixture was washed with 1N HCl and conc. NaHCO3 solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-6c91c108bd304162af4765ea8c8e70f4
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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