2,4-Dichloronitrobenzene → HCID 66821097, compound

HRID 1024706Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Cl[C:13]1[CH:18]=[C:17](Cl)[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:13]2[CH:18]=[C:17]([O:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:16]=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 5 °C

Procedure

4-cyanophenol 4.5 g (23.0 mmol), dissolved in 5 ml of DMF, was added to a stirred suspension of sodium hydride 0.92 g (23.0 mmol) in 5 ml of DMF cooled to 5° C. The reaction flask was stirred for 10 min at the same temperature and this was followed by dropwise addition (over 15 min) of 2,4-dichloronitrobenzene 2.0 g (10.5 mmol) dissolved in 5 ml of DMF. The reaction mixture was stirred for 6 h at 70° C. The reaction mass was poured into ice-cold water and extracted with 200 ml of ethylacetate. The organic phase was washed with 1 M Na2CO3 and saturated brine solution. The solution was dried over sodium sulphate and concentrated to afford an oily residue, which was purified by column chromatography using chlorofrom-ethyl acetate (10:2) to afford 2.5 g of the required product. 1H NMR (DMSO-d6): δ 6.79 (1H, d), 6.93 (1H, d), 7.06 (2H, d), 7.18 (2H, d), 7.75 (4H, d), 8.16 (1H, d).

Workup

stirringThe reaction mixture was stirred for 6 h at 70° C
additionThe reaction mass was poured into ice-cold water
extractionextracted with 200 ml of ethylacetate
washThe organic phase was washed with 1 M Na2CO3 and saturated brine solution
dry with materialThe solution was dried over sodium sulphate
concentrationconcentrated
customto afford an oily residue, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-d25f9442ec2c4314a801c0e697f94e0c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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