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

HRID 1849021노트

반응식

HRID 1849021 반응식
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]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 855731-Isopropylhydrazine hydrochlorideHCID 13488724ethyl (1Z)-N-ethoxycarbonylethanimidate

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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) follwed 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

후처리

  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)

출처 및 근거

ORD 기록
ord-ee721cbe99f44e76b51a40df006c6af3
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952043B2

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