Water → HCID 12833268, compound

HRID 848031Notes

Reaction equation

HRID 848031 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([NH:14][C:15](=[O:19])[CH2:16][CH2:17]Cl)[C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])([O-:5])=[O:4].O>CS(C)=O.O1CCCC1>[N+:3]([C:6]1[CH:7]=[C:8]([N:14]2[CH2:17][CH2:16][C:15]2=[O:19])[C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 12833267HCID 12833267, compound

Product 1

HCID 12833268HCID 12833268, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

5 g of sodium hydride (in the form of a 55% strength dispersion in oil) are stirred in 100 ml of dimethylsulphoxide until no further evolution of gas can be detected. 21.5 g (0.084 mol) of N-(3-nitro-4,6-dimethylphenyl)-β-chloropropionamide, suspended in 500 ml of tetrahydrofurane, are then added in the course of 5-10 minutes. The reaction temperature is kept at 15° for 1/2 an hour and water is then added dropwise in order to destroy excess sodium hydride. The reaction solution is taken up in methylene chloride and washed with water and saturated NaCl solution, dried (MgSO4) and evaporated. The crude product is subjected to fractional filtration on silica gel in chloroform. This gives 14.5 g (78%) of product; melting point 102°.

Workup

  1. additionare then added in the course of 5-10 minutes
  2. additionis then added dropwise in order
  3. customto destroy excess sodium hydride
  4. washwashed with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. filtrationThe crude product is subjected to fractional filtration on silica gel in chloroform

Sources & evidence

ORD record
ord-bb14318d576841cd876475a0afb4f339
Source dataset
uspto-grants-1981_10
Patent number
US04294606

Reaction notes

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