Nitrogen → HCID 18367420, compound

HRID 380137Notes

Reaction equation

HRID 380137 reaction equation
[H-].[Na+].[NH:3]=[C:4]1[NH:8][CH:7]([C:9]2[O:10][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH2:6][CH2:5]1.N#N.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Cl>CN(C)C=O>[NH:3]=[C:4]1[N:8]([CH2:33][C:32]2[CH:35]=[CH:36][CH:37]=[C:30]([O:29][CH3:28])[CH:31]=2)[CH:7]([C:9]2[O:10][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chlorideHCID 178507438HCID 178507438, compound

Product 1

HCID 18367420HCID 18367420, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (289 mg) was added to a stirred solution of 2-(5-imino-2-pyrrolidinyl)-4,5-diphenyloxazole (2.0 g) in N,N-dimethylformamide (20.0 ml) in the presence of an atmospheric N2 gas under ice cooling and the resulting mixture was stirred at the same temperature for 20 minutes and at room temperature for 1 hour 20 minutes. 3-Methoxybenzyl chloride (1.72 g) was added to the mixture under ice cooling and stirring was continued at room temperature overnight. The reaction mixture was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and aqueous sodium bicarbonate, dried over MgSO4, and evaporated in vacuo. The oily residue was chromatographed to afford 2-[5-imino-1-(3-methoxybenzyl)-2-pyrrolidinyl]-4,5-diphenyloxazole (1.80 g) as an amorphous powder.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe reaction mixture was partitioned between 1N hydrochloric acid and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and aqueous sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe oily residue was chromatographed

Sources & evidence

ORD record
ord-24e2a26ade8741af8ed472621c0a2b3a
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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