Triethylamine → HCID 25074336, compound

HRID 1944232Notes

Reaction equation

HRID 1944232 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](Cl)=[O:7].C([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([N:16]1[CH2:17][CH2:18][C:5]2[C:20](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=2)[CH2:19]1)=[O:7]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 870033,5-Dimethoxybenzoyl chloride

Product 1

HCID 25074336HCID 25074336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

B1 (345 mg, 1.5 mmol) and 3,5-dimethoxybenzoyl chloride (331 mg, 1.65 mmol) were dissolved in DCM (10 mL) and cooled to 0° C. Triethylamine (627 μL, 4.5 mmol) and the solution stirred for 30 minutes prior to warming to room temperature and stirring for 18 hours. The resultant solution was diluted with DCM and washed with NaHCO3 (sat.) and brine, dried over MgSO4 filtered and solvent evaporated under reduced pressure. Purification by column chromatography afforded B12 (146 mg, 31%). 1H NMR (270 MHz, CDCl3) δ 2.74-2.85 (2H, m), 3.58 and 3.91 (2H, m), 3.77 (3H, s), 4.48 and 4.77 (2H, s), 6.49-6.71 (5H, m), 6.72 and 6.98 (1H, d, J=7.7); HRMS (ESI+) calcd. for C18H20NO4 (M++H) 314.1387, found 314.1378; LC/MS (ES+) tr=2.09 min (>?%), m/z 314.3 (M++H); HPLC tr=1.476 min (>99%).

Workup

  1. temperatureto warming to room temperature
  2. washwashed with NaHCO3 (sat.) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated under reduced pressure
  6. customPurification by column chromatography
  7. customafforded B12 (146 mg, 31%)
  8. customLC/MS (ES+) tr=2.09 min (>?%), m/z 314.3 (M++H)
  9. custom=1.476 min (>99%)

Sources & evidence

ORD record
ord-41cd74d217f14fb38fb7dbab09d45d99
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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