Triethylamine → HCID 15307972, compound

HRID 1456229Notes

Reaction equation

HRID 1456229 reaction equation
Cl.[CH:2]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:25][C:26]1[CH:43]=[CH:42][CH:41]=[CH:40][C:27]=1[C:28]([NH:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)=[O:29]>ClCCl>[CH:2]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][N:7]([C:35]([C:34]3[CH:33]=[CH:32][C:31]([NH:30][C:28](=[O:29])[C:27]4[CH:40]=[CH:41][CH:42]=[CH:43][C:26]=4[CH3:25])=[CH:39][CH:38]=3)=[O:36])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27240145,6,11,12-Tetrahydrodibenz(b,f)azocinium chlorideHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Product 1

HCID 15307972HCID 15307972, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.245 g (1 mmol) of 5,6,11,-12-tetrahydrodibenz[b,f]azocine hydrochloride and 30 μl (2.2 mmol) of triethylamine in 2 ml of dichloromethane is added a solution of 0.281 g (1.1 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 4 ml of dichloromethane. The mixture is stirred overnight at room temperature, washed with water 2N HCl (3×2 ml) and 1N sodium bicarbonate (3×2 ml). The organic layer is dried (MgSO4) and filtered through a thin pad of hydrous magnesium silicate (pad washed with 3 volumes of CH2Cl2). The filtrate is concentrated to give 200 mg of a foam; Mass Spec-FAB 447(M+H).

Workup

  1. washwashed with water 2N HCl (3×2 ml) and 1N sodium bicarbonate (3×2 ml)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered through a thin pad of hydrous magnesium silicate (pad washed with 3 volumes of CH2Cl2)
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-fb3b2726f9f4434688db218f7a6ebf40
Source dataset
uspto-grants-1998_12
Patent number
US05843952

Reaction notes

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