Diethyl Ether → HCID 178452347, compound

HRID 1012988Notes

Reaction equation

HRID 1012988 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].S=[C:7]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9][NH:8]1.C(OCC)C>CO>[OH:3][N:2]=[C:7]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9][NH:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86634883HCID 86634883, compound

Product 1

HCID 178452347HCID 178452347, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of hydroxylamine hydrochloride (2 eq.) in methanol was added to an equimolar methanolic solution of potassium hydroxide. Potassium chloride was filtered off and the filtrate was added to a solution of the above tert-butyl 5-thioxo-1,4-diazepane-1-carboxylate (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 over Na2SO4 and concentrated under reduced pressure to give, after trituration with ethyl ether, the title amidoxime. 1H NMR (300 MHz, CDCl3) δ 6.4-6.1 (bs, 1H), 5.8 (broad triplet, 1H), 3.6-3.5 (m, 4H), 3.35-3.22 (m, 2H), 2.5-2.4 (m, 2H), 1.45 (s, 9H); MS (ES) C10H19N3O3 requires 229. Found: 230 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-0e2ecdaacce44549a27405108995baed
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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