Triethylamine → HCID 178518989, compound

HRID 259670Notes

Reaction equation

HRID 259670 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[Cl:20][C:21]1[CH:22]=[C:23]([OH:31])[C:24](=[CH:29][CH:30]=1)[C:25]([NH:27]O)=[O:26]>O1CCCC1>[Cl:20][C:21]1[CH:30]=[CH:29][C:24]2[C:25]([OH:26])=[N:27][O:31][C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27818484-chloro-N,2-dihydroxybenzamide

Product 1

HCID 178518989HCID 178518989, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1'-carbonyldiimidazole (12.76 g, 78.5 mmol) and triethylamine (12.6 mL, 90 mmol) in tetrahydrofuran is slowly added to a refluxing suspension of 4-chlorosalicylohydroxamic acid (13.39 g, 71.4 mmol) in tetrahydrofuran. The reaction mixture is refluxed for 1 hour, cooled, concentrated in vacuo, diluted with water, acidified with concentrated hydrochloric acid (pH1) and filtered to obtain a solid. A solution of the solid in ether is extracted with saturated sodium hydrogen carbonate solution. The combined aqueous extracts are acidified with concentrated hydrochloric acid and the resultant precipitate is collected and dried overnight to give the title product as a white solid, mp 218°-219° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water
  5. filtrationfiltered
  6. customto obtain a solid
  7. extractionA solution of the solid in ether is extracted with saturated sodium hydrogen carbonate solution
  8. customthe resultant precipitate is collected
  9. customdried overnight

Sources & evidence

ORD record
ord-c78fb03cec5346b19591444f6aeb1248
Source dataset
uspto-grants-1996_06
Patent number
US05523278

Reaction notes

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