Morpholine → 4-Morpholino-2-nitrobenzonitrile

HRID 1431289Notes

Reaction equation

HRID 1431289 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CS(C)=O>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 969244-Chloro-2-nitrobenzonitrile

Product 1

HCID 134992654-Morpholino-2-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-2-nitrobenzonitrile (7.828 g, 42.9 mmol) and morpholine (4.49 mL, 51.5 mmol) in DMSO (20.00 mL) was stirred at rt for 1 h, after which time LC-MS indicated a small amount of desired product formed. The reaction was heated to 100° C. After 24 h the reaction was equilibrated to rt and poured into 50 mL ea 1N aq. hydrochloric acid and EtOAc. The resulting orange precipitate was collected by filtration, rinsing with EtOAc, then dried under vacuum. Mass Spectrum (ESI) m/e=234.1 (M+1).

Sources & evidence

ORD record
ord-e1e7caa7668d43da8f0fc115ec48bf8e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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