Glycine → HCID 54145171, compound

HRID 1756474Notes

Reaction equation

HRID 1756474 reaction equation
O[CH2:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1.[NH2:12][CH2:13][C:14]([OH:16])=[O:15].[C:17]1(C)[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[N:3]1([CH2:2][N:12]([CH2:2][N:3]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:5]=[N:4]2)[CH2:13][C:14]([OH:16])=[O:15])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1

Participants

5

Reactant 3

HCID 750GlycineHCID 6101p-Toluenesulfonic acidHCID 2241691H-Benzotriazole-1-methanol

Product 1

HCID 54145171HCID 54145171, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

One hundred nineteen and three tenths parts of 1-(Hydroxymethyl) benzotriazole and glycine (30 parts) were added to 600 parts of dry toluene containing 1.7 parts of p-toluenesulfonic acid. The mixture was stirred and refluxed under a Dean-Stark trap. After about 4.5 hours, the theoretical amount of water (14.4 parts) had collected and heating was suspended. The reaction mixture was cooled in ice-water and the tan solid that had formed was filtered with suction. After washing the filter-cake consecutively with toluene and ether and drying it in vacuo, 116 parts of N,N-bis(benzotriazol-1-yl methyl) glycine were obtained and identified by 1H and 13C NMR spectral analysis. The product melted at 163°-6° C. and was obtained in 86% yield.

Workup

  1. temperaturerefluxed under a Dean-Stark trap
  2. customthe theoretical amount of water (14.4 parts) had collected
  3. temperatureheating
  4. temperatureThe reaction mixture was cooled in ice-water
  5. customthe tan solid that had formed
  6. filtrationwas filtered with suction
  7. washAfter washing the
  8. filtrationfilter-cake consecutively with toluene and ether
  9. dry with materialdrying it in vacuo, 116 parts of N,N-bis(benzotriazol-1-yl methyl) glycine
  10. customwere obtained

Sources & evidence

ORD record
ord-8919a15b7ad04511a24159f8bfdbf553
Source dataset
uspto-grants-1995_08
Patent number
US05441563

Reaction notes

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