Triethylamine → N-(3-pyridylmethyl)-4-[2-benzyloxybenzylthio]benzamide

HRID 355782Notes

Reaction equation

HRID 355782 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH2:16]([O:23][C:24]1[CH:40]=[CH:39][CH:38]=[CH:37][C:25]=1[CH2:26][S:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([S:27][CH2:26][C:25]3[CH:37]=[CH:38][CH:39]=[CH:40][C:24]=3[O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:36][CH:35]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 226755374-[2-Benzyloxybenzylthio]benzoylchloride

Product 1

HCID 18789574N-(3-pyridylmethyl)-4-[2-benzyloxybenzylthio]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 3-aminomethylpyridine (324 mg) and triethylamine (1.51 g) in dichloromethane (20 ml) at 0° C. was added 4-[2-benzyloxybenzylthio]benzoylchloride in CH2Cl2 (10 ml) (3 mmol). The mixture was allowed to warm to ambient temperature, washed with saturated aqueous NaHCO3 (3×20 ml), dried (MgSO4), filtered and evaporated. The residue was triturated with diethyl ether (20 ml) and crystallised from ethyl acetate to give N-(3-pyridylmethyl)-4-[2-benzyloxybenzylthio]benzamide (220 mg). (mpt. 108° C.).

Workup

  1. washwashed with saturated aqueous NaHCO3 (3×20 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was triturated with diethyl ether (20 ml)
  6. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2caed7bfce924563831bc1474f2bbdea
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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