Salicylic Acid → HCID 21520613, compound

HRID 1282945Notes

Reaction equation

HRID 1282945 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Cl:11][C:12]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=1[OH:19].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[Cl:11][C:12]1[CH:17]=[C:16]([CH:15]=[CH:14][C:13]=1[OH:19])[NH:18][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 10868DicyclohexylcarbodiimideHCID 775784-Amino-2-chlorophenol

Product 1

HCID 21520613HCID 21520613, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Salicylic acid (1.38 g.) and 2-chloro-4-aminophenol (1.44 g.) were dissolved in acetonitrile (130 ml.), to which with stirring was added as a dehydrating agent dicyclohexyl carbodiimide (1.88 g.) and stirring was continued for about an hour. The precipitated dicyclohexylurea was filtered off, rinsed with warm acetone (90 ml.), and the filtrate and the rinse were combined and evaporated to dryness under reduced pressure. A light brown powder (2.57 g.) of 3'-chloro-2,4'-dihydroxybenzanilide was obtained which was purified through column chromatography using silica-gel (Mallinkrodt Co., U.S.A.) and an ethyl acetate-methanol mixture as the elution solvent system to give needle-like crystals (0.18 g.) of 3'-chloro-2,4'-dihydroxybenzanilide. Yield: 7%. The melting point: 172.5° 173.5° C.

Workup

  1. stirringstirring
  2. waitwas continued for about an hour
  3. filtrationThe precipitated dicyclohexylurea was filtered off
  4. washrinsed with warm acetone (90 ml.)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4090d7f8e447442284efbb0dda94b0ca
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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