Trimethyltin chloride → HCID 178519608, compound

HRID 322874Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:27])[CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]#[N:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn](Cl)(C)C.[N-:33]=[N+:34]=[N-:35].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:27])[CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]2[NH:35][N:34]=[N:33][N:20]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 1-(3-benzyloxyphenyl)-4-cyano-2-phenylbutan-1-one (2.2 g), toluene (80 mL), trimethyltin chloride (6.17 g) and sodium azide is stirred at 115° C. for 30 hours. The cooled reaction mixture is filtered and the insoluble material is washed with a little ethyl acetate. The combined filtrate plus washings are evaporated and the resulting orange oily solid (3 g) is subjected to flash chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (29:1 v/v), followed by crystallisation from a mixture of ethyl acetate and cyclohexane, to give 5-[4-(3-benzyloxyphenyl)-4-oxo-3-phenylbutyl]-1H-tetrazole (0.86 g), in the form of a white solid, m.p. 136-138° C. [Elemental analysis:- C,72.5;H,5.63; N,14.0%; Calculated:- C,72.3;H,5.56; N,14.1%].

Workup

customThe cooled reaction mixture
filtrationis filtered
washthe insoluble material is washed with a little ethyl acetate
customThe combined filtrate plus washings are evaporated
washeluting with a mixture of dichloromethane and methanol (29:1 v/v)
customfollowed by crystallisation from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record: ord-66daf81fd6c244ce9e7da2ed4c51e3e5
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Reaction notes

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