Dietylaminopropin → HCID 25221615, compound

HRID 451270Notes

Reaction equation

HRID 451270 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][C:24]#[CH:25])[CH3:21]>CCCCCCC.CCOC(C)=O>[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][C:24]#[C:25][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH3:21]

Participants

4

Reactant 2

HCID 20010DietylaminopropinHCID 11482693Benzonitrile, 4-[[(4-methylphenyl)sulfonyl]oxy]-

Product 1

HCID 25221615HCID 25221615, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-cyano-phenyl ester and diethyl-prop-2-ynyl-amine following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 6:4; yield (95.4 mg, 90%); 1H NMR δ (CDCl3): 7.58 (d, J=8.65 Hz, 2H), 7.49 (d, J=8.63 Hz, 2H), 3.64 (s, 2H), 2.61 (q, J=7.16 Hz, 4H), 1.11 (t, J=7.15 Hz, 6H); LCMS m/z: 212.

Workup

  1. customyield (95.4 mg, 90%)

Sources & evidence

ORD record
ord-752d74782a8c41c5b3656ca0e45bbff2
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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