Benzoyl chloride → HCID 19874961, compound

HRID 465637Notes

Reaction equation

HRID 465637 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:29])[CH2:15][NH:16][CH2:17][C:18]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH3:3].C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(OCC)(=O)C>[CH3:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:11])[CH3:12])[C:5]=1[NH:13][C:14](=[O:29])[CH2:15][N:16]([CH2:17][C:18]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:1]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 19874901HCID 19874901, compound

Product 1

HCID 19874961HCID 19874961, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 0.48 g of the product of Example 6 and excess triethylamine in ethyl acetate at room temperature was added 0.16 mL benzoyl chloride all at once. The reaction mixture was allowed to sit 4 days at room temperature. The solution was then diluted with ethyl acetate and washed with dilute HCl, NaHCO3, and NaCl solutions, dried over MgSO4, filtered, and concentrated to an oil which was crystallized from diethyl ether. The white solid was collected by filtration. 0.48 g (61%). NMR (CDCl3) δ 1.12 (12H, d), δ 1.6-2.15 (8H, m), δ 2.99 (2H, m), δ 3.27 (2H, bs), δ 3.80 (2H, bs), δ 6.20 (1H, bs) δ 7.04-7.42 (13H, m). IR (KBr) 3269, 2963, 2869, 1696, 1600, 1520, 1461, 1254, 1222, 703 cm-1.

Workup

  1. washwashed with dilute HCl, NaHCO3, and NaCl solutions
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil which
  5. customwas crystallized from diethyl ether
  6. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-fc818cecb95d4fa79755f8682eaf1f32
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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