Triethylamine → HCID 178495799, compound

HRID 78437

Reaction equation

HRID 78437 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[S:7][C:6]1=[NH:12].CCN(CC)CC.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C1COCC1>[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](/[N:12]=[C:6]1\[S:7][C:8]([CH3:11])=[C:9]([CH3:10])[N:5]\1[CH2:4][CH2:3][O:2][CH3:1])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 235422-Bromobenzoyl chlorideHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495799HCID 178495799, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 126A (0.20 g, 1.1 mmol) and Et3N (0.3 mL, 2.2 mmol) in 25 mL THF was added 2-bromobenzoyl chloride (Aldrich, 0.18 mL, 1.4 mmol). This mixture stirred at ambient temperature for 20 hours then was concentrated under reduced pressure and the residue was diluted with 10 mL EtOAc and washed with 5 mL NH4Cl. The layers were separated and the aqueous layer was extracted (2×5 mL EtOAc). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via recrystallization with 50% hexanes/EtOAc to afford 0.18 g of the title compound (0.49 mmol, 46% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.26 (s, 3H), 2.28 (s, 3H), 3.30 (s, 3H), 3.78 (t, J=5.1 Hz, 2H), 4.42 (t, J=5.1 Hz, 2H), 7.22 (dt, J=7.8, 1.7 Hz, 1H), 7.34 (dt, J=7.5, 1.4 Hz, 1H), 7.63 (dd, J=8.0, 1.2 Hz, 1H), 7.90 (dd, J=7.6, 1.9 Hz, 1H); MS (DCI/NH3) m/z 369, 371 (M+H)+; Anal. calculated for C15H17BrN2O2S: C, 48.79; H, 4.64; N, 7.59. Found: C, 48.84; H, 4.49; N, 7.40.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. additionthe residue was diluted with 10 mL EtOAc
  3. washwashed with 5 mL NH4Cl
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted (2×5 mL EtOAc)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified via recrystallization with 50% hexanes/EtOAc

Sources & evidence

ORD record
ord-717a73a7ce2e4746b43a194450136c9f
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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