Dichloromethane → HCID 15676626, compound

HRID 1653971Notes

Reaction equation

HRID 1653971 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]([C:13]1([CH3:30])[C:17](=[O:18])[NH:16][C:15]([C:19]2[N:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:20]=2[C:21]([O:23][CH3:24])=[O:22])=[N:14]1)([CH3:12])[CH3:11].C(Cl)Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([N:16]1[C:17](=[O:18])[C:13]([CH:10]([CH3:12])[CH3:11])([CH3:30])[N:14]=[C:15]1[C:19]1[N:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 13250633HCID 13250633, compound

Product 1

HCID 15676626HCID 15676626, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (42.1 mL, 0.363 mol) is added dropwise to a 0° C. solution of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid, methyl ester (50 g, 0.173 mol) and 4-dimethylaminopyridine (4.2 g, 0.0344 mol) in pyridine. The reaction mixture is stirred for 1 hour at 0° C. and 4 hours at room temperature. Concentration in vacuo gives a liquid that is dissolved into methylene chloride and washed sequentially with 2 normal hydrochloric acid and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a solid that upon trituration with ether gives the title compound as a white solid (46.2 g, 68%), mp 104°-106° C., identified by IR and NMR spectral analyses.

Workup

  1. concentrationConcentration in vacuo
  2. customgives a liquid that
  3. washwashed sequentially with 2 normal hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a solid that upon trituration with ether

Sources & evidence

ORD record
ord-b80e576084584681908e4d80c9eefa59
Source dataset
uspto-grants-1995_04
Patent number
US05405827

Reaction notes

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