1-Hydroxybenzotriazole → HCID 86720745, compound

HRID 2167693Notes

Reaction equation

HRID 2167693 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:14][NH:15][O:16][CH3:17].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.C(N(CC)CC)C.CN(C)C=O>[C:1]([C:5]1[S:9][C:8]([C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19786348HCID 19786348, compound

Product 1

HCID 86720745HCID 86720745, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a N,N-dimethylformamide (25 mL) solution of 5-tert-butyl-1,3-thiazole-2-carboxylic acid (2.5 g), N,O-dimethylhydroxylamine hydrochloride (2.0 g), WSC.HCl (3.9 g), HOBt.H2O (3.1 g) and triethylamine (7.1 g) were added, and the resultant was stirred at room temperature for 1 day. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the desiccant was filtered off. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→50/50) to obtain the title compound (3.1 g) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationthe desiccant was filtered off
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→50/50)

Sources & evidence

ORD record
ord-5f0977a9ae7e4b6f96608a7d580d4d31
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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