Ammonium → HCID 178420370, compound

HRID 2393723Notes

Reaction equation

[N:1]([CH2:4][CH2:5][N:6]=[N+:7]=[N-:8])=[N+:2]=[N-:3].[CH2:9]([Mg]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH4+]>C1COCC1>[CH2:9]([NH:3][N:2]=[N:1][CH2:4][CH2:5][N:6]=[N:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 1.12 g (10 mmoles) of 1,2-diazidoethane in 20 ml. of THF was cooled to -60° C. This solution was treated with 15 ml of 2.0M benzylmagnesium chloride in THF (30 mmoles) dropwise with stirring. The reaction mixture was allowed to come to room temperature slowly, and was then cooled again to -60° C., and 10 ml. of ammonium buffer (see preparation above) was added and the reaction was allowed to come to room temperature. The reaction mixture was mixed with 100 ml. of diethylether and the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was removed on a rotary evaporator. The pink residual oil was subjected to high vacuum overnight, which produced a pale yellow solid. This material was crystallized from ether/pentane (1:1) to produce 1.71 g of colorless powdery solid m.p. 73°-75° C. Spectroscopy (nmr and mass) were consistent with the structure.

Workup

customto come to room temperature
customto come to room temperature
additionThe reaction mixture was mixed with 100 ml
customof diethylether and the organic layer was separated
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed on a rotary evaporator
customwas subjected to high vacuum overnight, which
customproduced a pale yellow solid
customThis material was crystallized from ether/pentane (1:1)

Sources & evidence

ORD record: ord-05ec27ebb6194137b68abd64a8a7ea17
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808038

Reaction notes

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