Ammonia → HCID 20092860, compound

HRID 274251Notes

Reaction equation

HRID 274251 reaction equation
O=S(Cl)Cl.[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](O)=O.COCC[O:17][CH3:18].[NH3:19].[C:20]1([CH3:26])[CH:25]=[CH:24]C=[CH:22][CH:21]=1>>[CH3:26][C:20]1[CH:25]=[CH:24][C:10]([C:6]2[O:5][CH:9]=[CH:8][C:7]=2[C:18]([NH2:19])=[O:17])=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 1140TolueneHCID 69192-Furancarboxylic acidHCID 80711,2-DimethoxyethaneHCID 24386Thionyl Chloride

Product 1

HCID 20092860HCID 20092860, compound

Procedure

20 ml of SOCl2 are added to a solution of the 13.4 g of furanoic acid prepared above in 70 ml of toluene. The mixture is refluxed for 3 h and the excess SOCl2 and the toluene are then distilled to give an oil, which is reacted at 5° C. with a solution of 100 ml of 1,2-dimethoxyethane saturated with ammonia. The precipitate is filtered off and washed with water and then with isopropyl alcohol to give 7 g of white crystals of amide.

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. distillationthe excess SOCl2 and the toluene are then distilled
  3. customto give an oil, which
  4. filtrationThe precipitate is filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-2bb16e675ea448d5971c37ecd79f64d7
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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