Dimethylformamide → HCID 178502856, compound

HRID 422117Notes

Reaction equation

HRID 422117 reaction equation
[OH:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[NH:23]O)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=[NH:4].O[Li].O.S([O:34][CH3:35])(OC)(=O)=O.[CH3:36]N(C=O)C>>[CH3:36][O:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:22](=[NH:25])[NH:23][O:34][CH3:35])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=[NH:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 178513261HCID 178513261, compound

Product 1

HCID 178502856HCID 178502856, compoundYield 92%

Procedure

To a suspension of the amidoxime 3 (1 mmol) in DMF (15 mL) was added LiOH.H2O (6 mmol, in 3 mL H2O) followed by dimethyl sulfate (5 mmol). The reaction was kept stirring overnight after which it was poured onto ice/water and the precipitate was filtered, washed with water and dried to give the desired compound in 92% yield; mp 214-215° C. 1H NMR (DMSO-d6); δ 3.75 (s, 6H), 6.12 (d, J=3.6 Hz, 1H), 6.17 (d, J=3.6 Hz, 1H), 7.76-8.00 (m, 8H).

Workup

  1. additionwas poured onto ice/water
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a65eb12c08a7404baed4c261ef273fe4
Source dataset
uspto-grants-2012_01
Patent number
US08101636B2

Reaction notes

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