1-Hydroxybenzotriazole → HCID 67959191, compound

HRID 1404953Notes

Reaction equation

HRID 1404953 reaction equation
[NH2:1][C:2](=[O:14])[CH2:3][O:4][C:5]1[C:9]([Br:10])=[CH:8][S:7][C:6]=1[C:11](O)=[O:12].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[Br:10][C:9]1[C:5]2[O:4][CH2:3][C:2](=[O:14])[NH:1][C:11](=[O:12])[C:6]=2[S:7][CH:8]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride3×HCID 67959076HCID 67959076, compound

Product 1

HCID 67959191HCID 67959191, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-amino-2-oxoethoxy)-4-bromothiophene-2-carboxylic acid (50.5 g), 1-hydroxybenzotriazole 1 hydrate (24.4 g) and DMF (500 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34.5 g), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34.5 g), and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34.5 g), and the mixture was stirred at room temperature for 7 hr. The solvent was evaporated under reduced pressure, and water (500 mL) was added to the residue to give the title compound (38.8 g, 82.2%) as a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. stirringthe mixture was stirred at room temperature for 7 hr
  3. customThe solvent was evaporated under reduced pressure, and water (500 mL)
  4. additionwas added to the residue

Sources & evidence

ORD record
ord-c059402d6bd04ab7b4df07a956b529d8
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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