HCID 57545962, compound → HCID 57546197, compound

HRID 913904Notes

Reaction equation

HRID 913904 reaction equation
FC(F)(F)C1C=C(C=O)C2N([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])N=NC=2C=1.[F:24][C:25]([F:46])([F:45])[C:26]1[CH:27]=[C:28]([CH:43]=[O:44])[C:29]2[C:30]([CH:42]=1)=[N:31][N:32](COCC[Si](C)(C)C)[N:33]=2>>[F:46][C:25]([F:24])([F:45])[C:26]1[CH:27]=[C:28]([CH:43]=[O:44])[C:29]2[N:33]=[N:32][N:31]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:30]=2[CH:42]=1

Participants

3

Reactant 2

HCID 57545962HCID 57545962, compoundHCID 57546109HCID 57546109, compound

Product 1

HCID 57546197HCID 57546197, compound

Procedure

5-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-7-carbaldehyde and 6-(Trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-benzo[d][1,2,3]triazole-4-carbaldehyde and 6-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-4-carbaldehyde. To a solution of 5-(trifluoromethyl)-1H-benzo[d][1,2,3]triazole-7-carbaldehyde (700 mg, 2.027 mmol) and N-methyldicyclohexylamine (0.59 mL, 2.74 mmol) in tetrahydrofuran (6 mL) at 0° C. was added (2-(chloromethoxy)ethyl)trimethylsilane (0.45 mL, 2.53 mmol). After 30 min, the ice bath was removed and stirring continued for an additional 30 min. The reaction was poured into ether, washed with water (2×), then 1M potassium bisulfate, then water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (5%→25% ethyl acetate/hexanes) gave two fractions. Concentration of the first fraction gave a mixture of 5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-7-carbaldehyde and 6-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-benzo[d][1,2,3]triazole-4-carbaldehyde (600 mg) as an oil. Concentration of the second fraction gave 6-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-4-carbaldehyde (165 mg) as a tan solid. 6-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazole-4-carbaldehyde: 1H-NMR (CDCl3, 500 MHz) δ 10.92 (s, 1H), 8.29 (s, 1H), 8.21 (s, 1H), 6.12 (s, 2H), 3.59 (m, 2H), 0.91 (m, 2H), −0.07 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 187.9, 146.2, 133.3, 130.4 (q, J=34 Hz), 127.4, 123.4 (q, J=274 Hz), 121.5 (q, J=2.9 Hz), 113.8 (q, J=4.8 Hz), 68.0, 17.7, −1.4.

Workup

  1. customConcentration of the first fraction gave

Sources & evidence

ORD record
ord-0d6461e52c46428095f1f0d90a7ac556
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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