Triethylamine → HCID 57991631, compound

HRID 556034Notes

Reaction equation

HRID 556034 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[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.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([F:29])=[CH:31][CH:32]=2)=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991631HCID 57991631, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 50 ml eggplant-shaped flask were added 1.00 g (3.37 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1, 0.68 g (6.75 mmol) triethylamine, 30 mg (0.25 mmol) DMAP and 25 ml THF, and then added dropwise 0.53 g (3.37 mmol) p-fluorobenzoyl chloride dissolved in 5 ml THF. The resulting mixture was stirred at room temperature for 2 hours, elevated to 35-40° C. and allowed to react for 10 hours, filtrated, washed with THF, the mother liquid was concentrated under a reduced pressure to give a pale brown oily crude product, separated with 50 ml ethyl acetate and 10 ml 1N HCl, the organic layer separated was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product, which was recrystallized with ethyl acetate/petroleum ether (1:2) to obtain a 1.10 g product as a white solid in a yield of 78.0%, mp: 164-165 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.77 (3H, s, OCH3), 4.22 (2H, s, CH2), 6.76 (2H, d, J=7.84 Hz, ArH), 6.94 (2H, t, 3JFH=3JHH=8.40 Hz, ArH), 7.24˜7.36 (7H, m, ArH), 7.71 (2H, dd, 3JHH=7.56, 4JFH=5.32 Hz, ArH), 11.62 (1H, br, CONH); EI-MS m/e (%): 418.2 (M+, 100), 123.0 (86); HREI-MS Calcd. for C24H19FN2O2S: 418.1151. found: 418.1138. Anal. Calcd. for C24H19FN2O2S: C, 68.88; H, 4.58; N, 6.69. found: C, 68.77; H, 4.48; N, 6.84.

Workup

  1. customelevated to 35-40° C.
  2. customto react for 10 hours
  3. filtrationfiltrated
  4. washwashed with THF
  5. concentrationthe mother liquid was concentrated under a reduced pressure
  6. customto give a pale brown oily crude product
  7. customseparated with 50 ml ethyl acetate and 10 ml 1N HCl
  8. customthe organic layer separated
  9. washwas washed with saturated aqueous sodium bicarbonate solution
  10. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give a crude product, which
  14. customwas recrystallized with ethyl acetate/petroleum ether (1:2)

Sources & evidence

ORD record
ord-0ffb37184cc74c7887004c4a00012616
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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