Tributyltin azide → Methyl-{2-[2-(1H-tetrazol-5-yl)-ethoxy]-phenyl}-amine

HRID 661702Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH2:7][C:8]#[N:9].[N:14]([Sn](CCCC)(CCCC)CCCC)=[N+:15]=[N-:16].C([Al](CC)CC)C>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:1][NH:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH2:7][C:8]1[NH:16][N:15]=[N:14][N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(2-methylamino-phenoxy)-propionitrile (1.55 g, 8.8 mmol) and azidotributyltin (3.6 mL, 13.2 mmol) in toluene (30 mL) was added triethylaluminum (9.3 mL, 17.6 mmol, 1.9 M in toluene). The mixture was heated at 80° C. for 16 hrs. The mixture was diluted with water (100 mL) and ethyl acetate (200 mL). The ethyl acetate layer was separated and removed. The resulting methyl-{2-[2-(1H-tetrazol-5-yl)-ethoxy]-phenyl}-amine stayed in the aqueous solution and was used in the next step without purification. [M+H]+ 220.1; tR=0.388 min (method 1).

Workup

customThe ethyl acetate layer was separated
customremoved
customwas used in the next step without purification

Sources & evidence

ORD record: ord-32654e9cf67d43fe9fc185b4e27d720f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084614B2

Reaction notes

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