Dimethylformamide → HCID 14456868, compound

HRID 279782Notes

Reaction equation

HRID 279782 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[CH:9]([CH2:10]I)[CH2:8][C:7]1=[O:12].[CH3:19][N:20](C)C=O.[C-]#N.[Na+]>O>[C:19]([CH2:10][CH:9]1[N:6]([CH2:5][C:4]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:3]=2[O:2][CH3:1])[C:7](=[O:12])[CH2:8]1)#[N:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 14456867HCID 14456867, compound

Product 1

HCID 14456868HCID 14456868, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.2 g (3.3 millimoles) of 1-(2,4-dimethoxy-benzyl)-4-iodomethyl-2-azetidinone and 5 ml of dimethyl formamide is stirred with 0.35 g (7 millimoles) of sodium cyanide at room temperature for 48 hours. The solution is poured onto 30 ml of water and extracted five times with 20 ml of ether each. The etheral solution is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo. Thus 0.6 g of 4-cyanomethyl-1-(2,4-dimethoxy-benzyl)-2-azetidinone are obtained. Yield: 70%.

Workup

  1. extractionextracted five times with 20 ml of ether each
  2. dry with materialThe etheral solution is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-7f060409e59a45c5ae2a43fc44b3b30b
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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