Benzoyl chloride → HCID 58526171, compound

HRID 1184984Notes

Reaction equation

HRID 1184984 reaction equation
[CH:1]1([NH:7][C:8]([O:16][N:17]2[C:22]([CH3:24])([CH3:23])[CH2:21][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:19][C:18]2([CH3:30])[CH3:29])=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[C:38]([N:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:8]([O:16][N:17]1[C:18]([CH3:30])([CH3:29])[CH2:19][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:21][C:22]1([CH3:24])[CH3:23])=[N:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58526184HCID 58526184, compound

Product 1

HCID 58526171HCID 58526171, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 1 (4.21 g, 10 mmol) [prepared according to Example 1] in toluene (25 ml) is added triethylamine (1.55 ml, 11 mmol) and benzoyl chloride (1.55 g, 11 mmol). The mixture is stirred at room temperature for 24 hours, then washed with water (2×10 ml), dried over MgSO4 and evaporated. The residue is chromatographed over silica gel with hexane-ethyl acetate (4:1) and the pure fractions are recristallized from acetonitrile to afford 0.98 g of the title compound as a white solid, mp. 147-152° C.

Workup

  1. washwashed with water (2×10 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue is chromatographed over silica gel with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-80681cf178b84f43a997c76d7d7a67cb
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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