Acetyl chloride → HCID 22467479, compound

HRID 1934716Notes

Reaction equation

HRID 1934716 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8](=[O:24])[C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[NH:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>ClCCl>[C:34]([NH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8](=[O:24])[C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[NH:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1)(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22467467HCID 22467467, compound

Product 1

HCID 22467479HCID 22467479, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(4-aminobenzyl)-2-(cyclopentylamino)-5-nitrobenzamide (126 mg) and triethylamine (0.119 mL) in anhydrous dichloromethane (20 mL) was added acetyl chloride (33.5 mg). After stirring for 2 hours at ambient temperature, the mixture was washed with an aqueous saturated sodium bicarbonate solution, water and brine. The resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with 10% methanol in chloroform. The obtained product was triturated with diisopropyl ether to give N-(4-acetamidobenzyl)-2-(cyclopentylamino)-5-nitrobenzamide as yellow powders (135 mg).

Workup

  1. washthe mixture was washed with an aqueous saturated sodium bicarbonate solution, water and brine
  2. dry with materialThe resultant was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 10% methanol in chloroform
  6. customThe obtained product was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-108ff3659c954ef381f811f734afa1a4
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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