Ammonia → 3,5-Dichloro-2-hydroxybenzamide

HRID 329193Notes

Reaction equation

HRID 329193 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:4]([C:5](OC)=[O:6])[C:3]=1[OH:13].[NH3:14]>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:4]([C:5]([NH2:14])=[O:6])[C:3]=1[OH:13]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 82082Benzoic acid, 3,5-dichloro-2-hydroxy-, methyl ester

Product 1

HCID 125631993,5-Dichloro-2-hydroxybenzamide

Conditions

Temperature
25 °C

Procedure

A 1 liter Parr autoclave was charged with 221 g. (1 mole) -dichlorophenyl)- of methyl 3,5-dichlorosalicylate and 140 g. (8 moles) of anhydrous ammonia. The mixture was stirred at 25° C for 24 hours. After venting excess ammonia, the product was ground to a fine powder and triturated with boiling chloroform. The mixture was filtered while hot and the residue weighed 153 g. Analysis by infrared, gas chromatography, and nuclear magnetic resonance confirmed that the product was 3,5-dichlorosalicylamide.

Workup

  1. additionA 1 liter Parr autoclave was charged with 221 g
  2. customtriturated with boiling chloroform
  3. filtrationThe mixture was filtered while hot and the residue

Sources & evidence

ORD record
ord-a66591768d304c25bc90ad70e522d405
Source dataset
uspto-grants-1977_04
Patent number
US04020081

Reaction notes

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