1,2-Dichloroethane → HCID 66616681, compound

HRID 1889718Notes

Reaction equation

HRID 1889718 reaction equation
[CH2:1]([S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:34][C:35]1[CH:43]=[CH:42][C:38]([CH2:39][CH2:40][NH2:41])=[CH:37][CH:36]=1>CN(C=O)C.C(OCC)(=O)C.Cl>[F:34][C:35]1[CH:43]=[CH:42][C:38]([CH2:39][CH2:40][NH:41][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[C:11]([CH2:10][S:9][CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:12]=2)=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 4653p-FluorophenethylamineHCID 757711-HydroxybenzotriazoleHCID 58531532HCID 58531532, compound

Product 1

HCID 66616681HCID 66616681, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(phenethylthiomethyl)benzoic acid (0.5 g, 1.84 mmol) in DMF (8 mL) were added EDC (0.49 g, 2.57 mmol), HOBT (0.28 g, 1.84 mmol) and 4-fluorophenethylamine (0.24 mL, 1.84 mmol). The clear reaction mixture was stirred at rt for 2 h and diluted with ethyl acetate and 1 N aqueous HCl solution. The organic layer was separated, washed with brine and dried over MgSO4. The filtrate was concentrated in vacuo. The residue was dissolved in DCM and purified by flash chromatography on silica gel eluting with 20% ethyl acetate in dichloromethane to give the desired product (0.34 g, 47%) as a white solid. 1H NMR (CDCl3) δ 7.61 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.35 (t, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 2H), 7.20-7.11 (m, 5H), 6.97 (t, J=8.0 Hz, 2H), 6.11 (s, 1H), 3.69 (s, 2H), 3.67-3.63 (m, 2H), 2.94-2.79 (m, 4H), 2.63-2.61 (m, 2H). MS (ESI): 394.1 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM
  6. custompurified by flash chromatography on silica gel eluting with 20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-f6e794667ee647ef892a4d77695f1702
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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