Water → HCID 178475131, compound

HRID 1277725Notes

Reaction equation

HRID 1277725 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12]([OH:14])=O)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.[NH2:27][C:28]1[CH:36]=[CH:35][C:31]2[NH:32][N:33]=[N:34][C:30]=2[CH:29]=1.C1(N=C=NC2CCCCC2)CCCCC1.O>CN(C)C=O>[NH:32]1[C:31]2[CH:35]=[CH:36][C:28]([NH:27][C:12](=[O:14])[CH2:11][O:10][C:9]3[CH:8]=[CH:7][C:6]([NH:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:16][CH:15]=3)=[CH:29][C:30]=2[N:34]=[N:33]1

Participants

7

Reactant 5

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 23453299HCID 23453299, compoundHCID 178507366HCID 178507366, compound

Product 1

HCID 178475131HCID 178475131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-(2-acetylhydrazino)phenoxyacetic acid (1.1 g), N-hydroxybenzotriazole (1.0 g) and 5-aminobenzotriazole (0.67 g, 0.005 mole) in dry dimethylformamide (10 ml) was stirred at 0° under dry nitrogen. Dicyclohexylcarbodiimide (1.1 g) in dry dimethylformamide (5 ml) was added dropwise over 15 minutes and the reaction mixture was stirred for 1 hour at 0° and 4 hours at room temperature. The dicyclohexylurea which precipitated was filtered and dried (0.7 g) and the filtrate was stirred at 60° overnight, under nitrogen. The reaction mixture was cooled and an additional precipitate of dicyclohexylurea was filtered off (0.3 g). The filtrate was evaporated, the residue was triturated with boiling methanol (50 ml) and the solid which precipitated was filtered off and dried (0.7 g). The filtrate was cooled at 5° overnight and the solid which crystallized out was filtered off and dried (0.6 g). The two precipitates, which were identical by IR, were combined and recrystallized from methanol:acetonitrile to give the product was a beige-colored powder (1.0 g). NMR analysis indicates the presence of ca 0.3 mole of H2O.

Workup

  1. customThe dicyclohexylurea which precipitated
  2. filtrationwas filtered
  3. customdried (0.7 g)
  4. stirringthe filtrate was stirred at 60° overnight, under nitrogen
  5. temperatureThe reaction mixture was cooled
  6. filtrationan additional precipitate of dicyclohexylurea was filtered off (0.3 g)
  7. customThe filtrate was evaporated
  8. customthe residue was triturated with boiling methanol (50 ml)
  9. customthe solid which precipitated
  10. filtrationwas filtered off
  11. customdried (0.7 g)
  12. temperatureThe filtrate was cooled at 5° overnight
  13. customthe solid which crystallized out
  14. filtrationwas filtered off
  15. customdried (0.6 g)
  16. customThe two precipitates
  17. customrecrystallized from methanol
  18. customacetonitrile to give the product

Sources & evidence

ORD record
ord-a24d134f75b945dcb50693f47eae3aeb
Source dataset
uspto-grants-1981_07
Patent number
US04278748

Reaction notes

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