Sodium hydride → HCID 16086969, compound

HRID 1724116Notes

Reaction equation

HRID 1724116 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)=[O:6].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31]>O(CCCC)CCCC>[CH3:23][O:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:12][CH:11]=2)[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[CH:15][CH:16]=1)=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 898486-Bromohexanoyl chlorideHCID 16086947HCID 16086947, compound

Product 1

HCID 16086969HCID 16086969, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil; 77.1 mg, 1.93 mmol) in anhydrous n-Bu2O (5 ml) 15a (500 mg, 1.75 mmol) is added batch wise, and the mixture is stirred for an additional two hours at RT. Then, 6-bromohexanoic acid chloride (0.314 ml, 2.10 mmol) is added, and the reaction is heated for 4 h under reflux. The mixture is allowed to cool to RT, poured into ice-water, and extracted with CH2Cl2. The organic phases are unified, washed with a saturated solution of NaHCO3 (2×) and saturated NaCl, and dried over MgSO4. Finally, the solvent is distilled off, and the crude product is crystallized from methanol. 713 mg (88%) of the desired compound 19a are obtained as a colorless solid. Melting point. 133-135° C.; IR (KBr) 2920, 1700, 1645, 1580 cm−1; 1H-NMR (CDCl3) δ 8.06 (d, 8.6 Hz, 4H), 7.30 (d, 8.6 Hz, 4H), 3.92 (s, 6H), 3.38 (t, 6.7 Hz, 2H), 2.29 (t, 7.4 Hz, 2H), 1.88-1.77 (m, 2H), 1.76-1.64 (m, 2H), 1.49-1.35 (m, 2H); MS (FD) m/z 464 (M++1 for Br81), 462 (M++1 for Br79).

Workup

  1. additionis added batch wise
  2. temperaturethe reaction is heated for 4 h
  3. temperatureunder reflux
  4. temperatureto cool to RT
  5. extractionextracted with CH2Cl2
  6. washwashed with a saturated solution of NaHCO3 (2×) and saturated NaCl
  7. dry with materialdried over MgSO4
  8. distillationFinally, the solvent is distilled off
  9. customthe crude product is crystallized from methanol

Sources & evidence

ORD record
ord-faeed08c17e94a6e8f4873704a19329a
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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