1-Chloro-4-(phenylethynyl)benzene → HCID 24954859, compound

HRID 216006Notes

Reaction equation

C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[NH:14][NH:15][NH:16][C:25]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 3483091-Chloro-4-(phenylethynyl)benzene

HCID 4984872Tributyltin azide

Product 1

HCID 24954859HCID 24954859, compoundYield 54%

Conditions

Temperature: 150 °C

Procedure

A mixture of tri-n-butyltin azide (0.86 mL, 3.15 mmol) with the 4-chlorophenylethynylbenzene (3 mmol) was heated at 150° C. for 70 h in a sealed glass bottle. The resulting solution was purified by column chromatography (cyclohexane/AcOEt, 5:1) and recrystallized from (cyclohexane/AcOEt) to give 4-(p-chlorophenyl)-5-phenyl-1H(2H)-[1,2,3]triazole as a white solid (413 mg, 54% yield); m.p. 124-126° C. 1H NMR (200 MHz, CDCl3, 25° C.) δ=7.51-7.46 (m, 4H), 7.38-7.35 (m, 3H), 7.31 (dt, 3J=8.6 Hz, 4J=5J=2.2 Hz, 2H) ppm. ES-MS: m/z=278 [M++Na], 256 [M+]. C14H10ClN3 (255.70): caldc. C, 65.76; H, 3.94; N, 16.43. found C, 65.93; H, 3.84; N, 16.37.

Workup

customThe resulting solution was purified by column chromatography (cyclohexane/AcOEt, 5:1)
customrecrystallized from (cyclohexane/AcOEt)

Sources & evidence

ORD record: ord-f806dd038a394b3da621626581624893
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193223B2

Reaction notes

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