1H-Benzotriazole-1-carboxaldehyde → HCID 13405074, compound

HRID 517695Notes

Reaction equation

HRID 517695 reaction equation
[N:1]1([CH:10]=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2N=N1.[F:12][C:13]([F:23])([F:22])[O:14]C1C=CC(N)=CC=1>O1CCCC1>[F:12][C:13]([F:23])([F:22])[O:14][C:8]1[CH:7]=[CH:6][C:5]([NH:1][CH:10]=[O:11])=[CH:4][CH:9]=1

Participants

4

Reactant 2

HCID 5767401H-Benzotriazole-1-carboxaldehyde2×HCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 13405074HCID 13405074, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1H-1,2,3-benzotriazole-1-carbaldehyde (299 mg, 2.032 mmol, Sigma-Aldrich) was added to a solution of 4-[(trifluoromethyl)oxy]aniline (0.227 mL, 1.694 mmol) in tetrahydrofuran (THF) (6 mL). The solution was heated to 60° C. and stirred for 22.5 hours. 1H-1,2,3-benzotriazole-1-carbaldehyde (199 mg, 1.355 mmol) was added and the reaction mixture stirred for a further 20 hours before concentrating in vacuo. The resulting solid was dissolved in DCM (30 ml), washed with 2M HCl (15 ml), the organic layer was passed through a hydrophobic frit and reduced in vacuo. The crude material was purified by silica chromatography (Biotage SP4, eluting iso-hexane (5 column volumes) followed by a gradient from 0-20% EtOAc in iso-hexane (over 15 column volumes)) to yield the title compound as a white solid (0.338 g).

Workup

  1. stirringthe reaction mixture stirred for a further 20 hours
  2. concentrationbefore concentrating in vacuo
  3. dissolutionThe resulting solid was dissolved in DCM (30 ml)
  4. washwashed with 2M HCl (15 ml)
  5. customThe crude material was purified by silica chromatography (Biotage SP4
  6. washeluting iso-hexane (5 column volumes)

Sources & evidence

ORD record
ord-42cb617100cb475881ac19e6bcd67f7c
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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