Lawesson's reagent → HCID 22181432, compound

HRID 1796473Notes

Reaction equation

HRID 1796473 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH2:23]([O:25][C:26]1[CH:54]=[CH:53][C:29]([C:30]([C:32]2[N:36]([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:35]3[CH:42]=[CH:43][C:44]([C:46]([N:48]([CH2:51][CH3:52])[CH2:49][CH3:50])=O)=[CH:45][C:34]=3[N:33]=2)=[O:31])=[CH:28][CH:27]=1)[CH3:24]>C1(C)C=CC=CC=1>[CH2:23]([O:25][C:26]1[CH:54]=[CH:53][C:29]([C:30]([C:32]2[N:36]([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:35]3[CH:42]=[CH:43][C:44]([C:46](=[S:10])[N:48]([CH2:51][CH3:52])[CH2:49][CH3:50])=[CH:45][C:34]=3[N:33]=2)=[O:31])=[CH:28][CH:27]=1)[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22181310HCID 22181310, compound

Product 1

HCID 22181432HCID 22181432, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (0.0963 g, 0.238 mmol) was added to a stirred solution of 2-(4-ethoxybenzoyl)-N,N-diethyl-1-isopentyl-1H-benzimidazole-5-carboxamide (0.0451 g, 0.104 mmol) in dry toluene (5 mL) under an atmosphere of N2. The reaction was heated to reflux for 0.5 h, and then cooled to room temperature and concentrated. The residue was purified by column chromatography (3:1 Hexanes:EtOAc) to provide the title compound (0.0137 g, 29%) as a glassy yellow solid. 1H-NMR (CD3OD): δ 8.19 (d, J=9.2 Hz, 2H), 7.67 (d, J=8.4 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.06 (d, J=9.2 Hz, 21), 4.55 (dd, J=8.4 Hz, J=7.2 Hz, 2H), 4.17 (q, J=7.6 Hz, 4H), 3.53 (q, J=7.6 Hz, 2H), 1.80–1.71 (m, 2H), 1.71–1.58 (m, 1H), 1.44 (t, J=7.6 Hz, 3H), 1.41 (t, J=7.6 Hz, 3H), 1.17 (t, J=7.6 Hz, 3H), 0.97 (d, J=6.4 Hz, 6H). 13C-NMR (CD3OD): δ 201.23, 185.95, 165.57, 149.55, 141.87, 141.18, 136.28, 134.64, 130.31, 124.56, 118.20, 115.41, 112.36, 65.15, 47.48, 44.89, 40.18, 27.20, 22.77, 14.95, 14.07, 11.44. MS (ESI) (M+H)+=452. Anal. Calcd for C26H33N3O2S.0.3H2O: C, 68.33; H, 7.41; N, 9.19. Found: C, 68.44; H, 7.52; N, 9.01.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 0.5 h
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (3:1 Hexanes:EtOAc)

Sources & evidence

ORD record
ord-1d2488a5b3b6445198d4e5219a3b656f
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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