1-Hydroxybenzotriazole → HCID 60644837, compound

HRID 1506139Notes

Reaction equation

HRID 1506139 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:14]([O:15][CH3:16])[CH3:13])=[O:9])=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 763604-(Hydroxymethyl)benzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 60644837HCID 60644837, compoundYield 109.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-(Hydroxymethyl)benzoic acid (3.00 g, 19.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.31 g, 23.7 mmol) in chloroform (30 mL) was stirred with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.54 g, 23.7 mmol), 1-hydroxybenzotriazole (3.20 g, 23.7 mmol) and N,N-diisopropylethylamine (8.04 mL, 47.3 mmol) at room temperature for one day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a mixture containing the title compound as a colorless oil (4.20 g). The resulting mixture was used for the next step.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a mixture

Sources & evidence

ORD record
ord-d7aa171a93f44eceac09e69585585c35
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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