Tributyltin azide → HCID 178527851, compound

HRID 1735903Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]([CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[C:12]2=[S:26])=[CH:5][CH:4]=1)#[N:2].C([Sn]([N:40]=[N+:41]=[N-:42])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[NH:40]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]3[CH:15]=[CH:14][N:13]([CH:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17]4)[C:12]3=[S:26])=[CH:7][CH:8]=2)=[N:2][N:42]=[N:41]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture 3-[2-(4-cyanophenyl)ethyl]-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.5 g, 1.4 mmol), prepared as in Example 15, and tributyltin azide (1.39 g, 4.2 mmol) in 3 mL of xylene was heated at 120° C. under nitrogen for approximately 16 hours. The mixture was purified by chromatography on silica gel eluting with methylene chloride/methanol and the purified product was recrystallized from ethyl acetate/methanol to give 3-[2-(4 (1H)-tetrazol-5-ylphenyl)ethyl]-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.5 g, 1.4 mmol), m.p. 218°-220° C.

Workup

customThe mixture was purified by chromatography on silica gel eluting with methylene chloride/methanol
customthe purified product was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record: ord-564ee741486247a7b9d348502932bb8e
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05538988

Reaction notes

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