Dimethylformamide → HCID 57991628, compound

HRID 556108Notes

Reaction equation

HRID 556108 reaction equation
[CH2:1]([C:8]1[S:12][C:11](Cl)=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CN(C=O)C>O>[CH2:1]([C:8]1[S:12][C:11]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 168937Lithium hydroxide, monohydrateHCID 66986106HCID 66986106, compound

Product 1

HCID 57991628HCID 57991628, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To 25 ml eggplant-shaped bottle were added 1.00 g (3.17 mmol) 5-benzyl-2-chloro-4-(4-methoxy-phenyl)-thiazole prepared in the step 1, 0.27 g (6.34 mmol) LiOH.H2O, 20 mg KI, 0.55 g (6.34 mmol) morpholine, 5 ml DMF and 0.5 ml water. The mixture was stirred until homogeneous, heated to 100° C., stirred for 20 hours, added 20 ml water, and extracted with ethyl acetate 3×10 ml. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a thick crude product, which was purified under a reduced pressure by silica gel column chromatography eluted with petroleum ether and ethyl acetate at a ratio 4:1-3:1 (V:V) to give a 0.73 g product as a white solid in a yield of 62.9%, mp: 88-89 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.47 (4H, m, 2×CH2), 3.80 (4H, t, J=5.2 Hz, 2×CH2), 3.82 (3H, s, OCH3), 4.12 (2H, s, CH2), 6.92 (2H, d, J=8.40 Hz, ArH), 7.18˜7.32 (5H, m, ArH), 7.53 (2H, d, J=8.40 Hz, ArH); EI-MS m/e (%): 366.1 (M+, 100), 309.1 (23); HREI-MS Calcd. for C21H22N2O2S: 366.1402. found: 366.1404. Anal. Calcd. for C21H22N2O2S: C, 68.83; H, 6.05; N, 7.64. found: C, 68.73; H, 6.26; N, 7.83.

Workup

  1. stirringstirred for 20 hours
  2. extractionextracted with ethyl acetate 3×10 ml
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a thick crude product, which
  8. customwas purified under a reduced pressure by silica gel column chromatography
  9. washeluted with petroleum ether and ethyl acetate at a ratio 4:1-3:1 (V:V)

Sources & evidence

ORD record
ord-19fe70a0354342879c85f6afd5294384
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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