Benzyl Bromide → 2-(5-Acetyl-2-ethylamino-phenylimino)-3,5-dibenzyl-thiazolidin-4-one

HRID 600830Notes

Reaction equation

HRID 600830 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:24][CH2:25][CH3:26])=[C:8]([N:10]=[C:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:23])[CH2:13][S:12]2)[CH:9]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:24][CH2:25][CH3:26])=[C:8]([N:10]=[C:11]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:14](=[O:23])[CH:13]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[S:12]2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 219375832-(5-Acetyl-2-ethylaminophenylimino)-3-benzylthiazolidin-4-one

Product 1

HCID 115833862-(5-Acetyl-2-ethylamino-phenylimino)-3,5-dibenzyl-thiazolidin-4-oneYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-thiazolidin-4-one (0.11 g, 0.30 mmol) in THF (3 mL, anhyd) chilled to 0° C. was added dropwise 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (0.30 mL, 0.30 mmol). After 5 min benzyl bromide (36 μL, 0.30 mmol) was added to the reaction mixture, which was stirred at 0° C. for 2 h and then allowed to warm to ambient temperature. After 1 h the reaction mixture was quenched with satd NH4Cl and extracted with EtOAc. The organic layer was isolated, washed with brine, dried over anhyd Na2SO4, concentrated and chromatographed (silica gel, 0:100 to 20:80 EtOAc-Hex) to yield the title product (11 mg) as a white solid. 1H-NMR (CDCl3): δ 7.66 (1H, dd, J=8.5 Hz, 2.0 Hz), 7.49 (1H, d, J=2.0 Hz), 7.19-7.35 (10H, m), 6.48 (1H, d, J=8.5 Hz), 5.00 (2H, m), 4.48 (1H, dd, J=9.0 Hz, 3.8 Hz), 3.92 (1H, hr t), 3.53 (1H, dd, J=14.1 Hz, 3.8 Hz), 3.17 (1H, dd, J=14.1 Hz, 9.0 Hz), 3.02 (2H, m), 2.47 (3H, s), 1.02 (3H, t); MS (ESI): 458 (MH+).

Workup

  1. temperatureto warm to ambient temperature
  2. customAfter 1 h the reaction mixture was quenched with satd NH4Cl
  3. extractionextracted with EtOAc
  4. customThe organic layer was isolated
  5. washwashed with brine
  6. dry with materialdried over anhyd Na2SO4
  7. concentrationconcentrated
  8. customchromatographed (silica gel, 0:100 to 20:80 EtOAc-Hex)

Sources & evidence

ORD record
ord-b9e597b08b6b497eb8d24e603ce79c0f
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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