Diisopropylethylamine → HCID 67335821, compound

HRID 451445Notes

Reaction equation

HRID 451445 reaction equation
[Br:1][C:2]1[C:3]([NH:11][C:12]([NH:14]C(OCC)=O)=S)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:7]=1.Cl.NO.C([N:26](C(C)C)CC)(C)C>CO>[Br:1][C:2]1[C:3]2[N:4]([N:26]=[C:12]([NH2:14])[N:11]=2)[CH:5]=[C:6]([CH:8]2[CH2:9][CH2:10]2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86656220Carbamic acid, N-[[(3-bromo-5-cyclopropyl-2-pyridinyl)amino]thioxomethyl]-, ethyl ester

Product 1

HCID 67335821HCID 67335821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-bromo-5-cyclopropyl-pyridin-2-yl)-N′-ethoxycarbonyl-thiourea (1.5 g, 4.36 mmol) in dry methanol (20 mL) were added hydroxylamine hydrochloride (1.41 g, 21.8 mmol) and diisopropyl ethylamine (12.14 mL, 13.08 mmol) under an argon atmosphere and stirred at room temperature for 6 hours. Methanol was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as off white solid (910 mg, 82%).

Workup

  1. customMethanol was evaporated
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-25156a17f87648fba09974a995f6a362
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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