Triethylamine → HCID 15307972, compound

HRID 1957644Notes

Reaction equation

HRID 1957644 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH3:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[C:11]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)=[O:12]>ClCCl>[CH:16]1[C:7]2[CH2:23][CH2:24][C:25]3[CH:26]=[CH:9][CH:10]=[CH:11][C:5]=3[CH2:4][N:3]([C:18]([C:17]3[CH:21]=[CH:22][C:14]([NH:13][C:11](=[O:12])[C:10]4[CH:23]=[CH:24][CH:25]=[CH:26][C:9]=4[CH3:8])=[CH:15][CH:16]=3)=[O:19])[C:6]=2[CH:22]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Product 1

HCID 15307972HCID 15307972, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.245 g (1 mmol) of 5,6,-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-9a66434c284c47f6b9086e09948ededd
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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