Ammonia → Benzamide

HRID 1277344Notes

Reaction equation

HRID 1277344 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[OH-].C([Sn+2]Cl)CCC.[NH3:18]>>[C:1]([NH2:18])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 243Benzoic AcidHCID 2204194713355-96-9

Product 1

HCID 2331Benzamide

Conditions

Temperature
165 °C

Procedure

To demonstrate the ability to conduct the amidation in an inert reaction medium 400 gms. benzoic acid was dissolved in 400 mls. mineral spirits with 2 gms. butylchlorotin dihydroxide. The solution was then heated with agitation to 165° C. while introducing ammonia below the surface ofthe liquid through a dispersion tube at a rate of 0.5 SCFH. As the reactionprogressed the amide product came out of solution. An acid value of 12 was achieved after only 7 hours reaction. At the completion of the reaction the insoluble amide product was recovered by filtration, washed and dried.Benzamide (melt point 133°-135° C.) obtained by this process is substantially free of undesirable nitrile by-product.

Workup

  1. customreaction
  2. filtrationwas recovered by filtration
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-1c73950008ff47ea99dc188e6e1a116b
Source dataset
uspto-grants-1981_07
Patent number
US04277410

Reaction notes

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