Triethylamine → Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate

HRID 1613120Notes

Reaction equation

HRID 1613120 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:7]2[NH:8][N:9]=[N:10][C:6]=2[CH:5]=1.CC(N(C)C)=O.C(N(CC)CC)C.[C:26](Cl)(=[O:34])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>N1C=CC=CC=1>[O:27]([C:26]([NH:3][C:4]1[CH:12]=[CH:11][C:7]2[NH:8][N:9]=[N:10][C:6]=2[CH:5]=1)=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31374DimethylacetamideHCID 178478652HCID 178478652, compound

Product 1

HCID 178521835Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamateYield 88.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To 62.1 g of 5-aminobenzotriazole dihydrochloride was added 500 ml of dimethylacetamide, and 83,7 ml of triethylamine was added dropwise thereto while being cooled in an ice bath. To the mixture was further added dropwise 21.0 ml of pyridine, and 42.3 g of phenyl chlorocarbonate was then added dropwise thereto while maintaining the system at 5° C. or lower, followed by stirring at room temperature for 2 hours. After the reaction, the reaction mixture was poured into 2 (of ice-water for crystallization, followed by filtration to obtain 60.8 g of 5-phenoxycarbonylaminobenzotriazole.

Workup

  1. additionwas added dropwise
  2. temperaturewhile being cooled in an ice bath
  3. additionwas then added dropwise
  4. customAfter the reaction
  5. customfor crystallization
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-015a1ffb1aa041e18734c98a8082ceec
Source dataset
uspto-grants-1993_03
Patent number
US05192647

Reaction notes

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