Diisopropyl Ether → [3-(3-Dimethoxymethyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester

HRID 1968807Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:21][CH3:22])[C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:7][C:8]1[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1.C(OC(C)C)(C)C.[C:30]1([CH2:36][O:37][C:38](Cl)=[O:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:36]([O:37][C:38](=[O:39])[NH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:4]([CH:3]([O:2][CH3:1])[O:21][CH3:22])[CH:5]=2)[CH:9]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 3-(3-dimethoxymethyl-4-nitro-phenoxy)-phenylamine (0.14 mol), prepared as in Example 65, and diisopropyl ether (0.16 mol) in DCM (1000 mL) was cooled to 10° C., and carbonochloridic acid phenylmethyl ester (also known as benzyl chloroformate) (0.16 mol) was added dropwise, then the reaction mixture was stirred overnight at room temperature and washed with H2O. The organic layer was separated, dried (MgSO4), filtered off and the solvent was evaporated. The residue was purified by column chromatography (eluent: 100% CH2Cl2). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

additionwas added dropwise
washwashed with H2O
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered off
customthe solvent was evaporated
customThe residue was purified by column chromatography (eluent: 100% CH2Cl2)
customThe product fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-761f74c342b645c696abd893f8269a8e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426429B2

Reaction notes

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