Benzene, 1-(bromomethyl)-3-nitro- → (4-Isopropyl-phenyl)-[2-(3-nitro-benzylamino)-5-propargyloxy-phenyl]-methanone

HRID 445172Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:13].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br)([O-:25])=[O:24].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:3]2[CH:4]=[C:5]([O:8][CH2:9][C:10]#[CH:11])[CH:6]=[CH:7][C:2]=2[NH:1][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=2)=[O:13])=[CH:19][CH:18]=1)([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 30 g (102 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone, 23.8 g (110 mmol) 3-nitrobenzylbromide and 21 ml (120 mmol) Hünig's base in 160 ml methylene chloride is stirred overnight at 45° C. The resulting dark solution is washed twice with 200 ml water and with brine. Purification of the crude product by chromatography (CH2Cl2/petroleum ether 1:1) affords 34.4 g (79%) of a viscous red oil.

Workup

washThe resulting dark solution is washed twice with 200 ml water and with brine
customPurification of the crude product by chromatography (CH2Cl2/petroleum ether 1:1)

Sources & evidence

ORD record: ord-f6dc5ad0663a4197b0f8153817734f5c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476286B2

Reaction notes

Loading…