Diethyl Ether → HCID 178526320, compound

HRID 1013006Notes

Reaction equation

HRID 1013006 reaction equation
[NH2:1][OH:2].Cl.[OH-].[K+].[O:6]1[CH2:12][CH2:11][C:10](=S)[NH:9][CH2:8][CH2:7]1.C(OCC)C>CO>[O:6]1[CH2:12][CH2:11][C:10](=[N:1][OH:2])[NH:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 55287876HCID 55287876, compound

Product 1

HCID 178526320HCID 178526320, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of NH2OH HCl (2 eq.) in methanol was added to an equimolar methanolic solution of KOH. KCl was filtered off and the filtrate was added to a solution of 1,4-oxazepane-5-thione (1 eq.) in methanol. The mixture was stirred at 55° C. overnight, then cooled to room temperature and the solvent was removed under reduced pressure. The residue was taken in chloroform, washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give, after trituration with ethyl ether, the title compound. 1H NMR (300 MHz, CDCl3) δ 8.9 (bs, 1H), 6.15 (bs, 1H), 3.68-3.51 (m, 4H), 3.21-3.19 (m, 2H), 2.38-2.31 (m, 2H); MS (ES) C5H10N2O2 requires 130. Found: 131 (M+H+).

Workup

  1. filtrationKCl was filtered off
  2. temperaturecooled to room temperature
  3. customthe solvent was removed under reduced pressure
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give

Sources & evidence

ORD record
ord-3524c95402de490c8d407e696f8de643
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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