Dimethylamine → HCID 58493986, compound

HRID 2360506Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11])([CH3:4])([CH3:3])[CH3:2].[C:19](N1C=CN=C1)([N:21]1C=CN=[CH:22]1)=O.CNC>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-:18])=[O:17])[C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([N:21]([CH3:22])[CH3:19])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

44 g 5-tert-butyl-2-methoxy-3-nitro-benzoic acid are dissolved in 400 ml of tetrahydrofuran, combined with 31 g carbonyldiimidazole and stirred for 2 hours at 50° C. The mixture is cooled to ambient temperature, combined with 173 ml of a 2 M solution of dimethylamine in tetrahydrofuran and stirred for a further 16 hours at 50° C. Then it is diluted with ethyl acetate and washed successively with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel with chloroform.

Workup

temperatureThe mixture is cooled to ambient temperature
stirringstirred for a further 16 hours at 50° C
washwashed successively with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
dry with materialAfter drying with sodium sulphate the solvents
customthe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record: ord-850b76939ec04e9a91655bc2b9e2d921
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686022B2

Reaction notes

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