Benzyl azide → HCID 66958038, compound

HRID 1424685Notes

Reaction equation

HRID 1424685 reaction equation
[I:1][C:2]#[C:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.[CH2:9]([N:16]=[N+:17]=[N-:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[I:1][C:2]1[N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=[N:18][C:3]=1[C:4]1[CH:8]=[CH:7][S:6][CH:5]=1

Participants

3

Reactant 2

HCID 12152Benzyl azideHCID 66958011HCID 66958011, compound

Product 1

HCID 66958038HCID 66958038, compound

Procedure

Synthesized from 3-(iodoethynyl)thiophene and benzylazide using one-pot/two-step general procedure, 1.24 g, 3.38 mmol, 81%; mp=125-127° C. (dec.); IR (υ[cm−1]) 3025, 1496, 1455, 1354, 1318, 1230, 1211, 1072, 1008, 783, 717; 1H NMR (600 MHz, CDCl3) δ=7.94 (d, J=1.6, 1H), 7.75 (d, J=4.7, 1H), 7.39 (dd, J=4.7, 3.0, 1H), 7.36-7.29 (m, 3H), 7.29-7.25 (m, 2H), 5.64 (s, 2H); 13C NMR (151 MHz, CDCl3) δ=147.3, 134.5, 131.2, 129.1, 128.7, 127.9, 126.8, 126.1, 122.9, 76.0, 54.5; HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C13H11IN3S, 367.9713; found 367.9713.

Sources & evidence

ORD record
ord-7f251bb37527469782dc083ed4b8c7b6
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

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