Triethylamine → 3-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 707841ノート

反応式

HRID 707841 の反応式
C([O:3][C:4](=O)/[N:5]=[C:6](\OCC)/[CH3:7])C.Cl.[CH:13]([NH:16][NH2:17])([CH3:15])[CH3:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:13]([N:16]1[C:4](=[O:3])[NH:5][C:6]([CH3:7])=[N:17]1)([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 855731-Isopropylhydrazine hydrochlorideHCID 13488724ethyl (1Z)-N-ethoxycarbonylethanimidate

生成物 1

HCID 1363405273-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of [1-ethoxy-eth-(Z)-ylidene]-carbamic acid ethyl ester (834 mg, 5.24 mmol) in toluene (15 mL) was added isopropyl hydrazine hydrochloride (637 mg, 5.76 mmol) followed by triethylamine (803 μL, 5.76 mmol). The reaction vessel was sealed and stirred at 45° C. for 45 minutes before the addition of triethylamine (803 μL, 5.76 mmol). The resultant mixture was heated to 90° C. and stirred for 17 hours, then cooled and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM) to give 2-Isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one as an off white solid (329 mg, 44%). LCMS: RT=2.16 min, [M+Na]+=164

後処理

  1. customThe reaction vessel was sealed
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM)

出典と根拠

ORDレコード
ord-91de88b466dd433ebc901c92b0909ae0
出典データセット
uspto-grants-2015_11
特許番号
US09175009B2

反応ノート

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