Hydrochloric Acid → 2,2,2-Trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1h-pyrazol-5-ylcarbamate

HRID 1930339

반응식

HRID 1930339 반응식
[CH:1]([N:4]1[C:8](C(O)=O)=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:3])[CH3:2].C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[CH:41](Cl)([OH:45])[CH:42]([Cl:44])[Cl:43].[ClH:47]>O1CCOCC1>[CH:1]([N:4]1[C:8]([NH:19][C:22](=[O:31])[O:45][CH2:41][C:42]([Cl:44])([Cl:43])[Cl:47])=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:2])[CH3:3]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1194271,1,2-TrichloroethanolHCID 199401P,P-Diphenylphosphinic azideHCID 690359331-isopropyl-3-(thiophen-2-yl)-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 690364842,2,2-Trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1h-pyrazol-5-ylcarbamate수율 80%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazole-5-carboxylic acid (0.68 g, 2.9 mmol) in dioxane (10 mL) was added with triethylamine (0.44 g, 4.3 mmol), diphenylphosphorylazide (0.95 g, 3.5 mmol) and trichloroethanol (0.86 g, 5.8 mmol) and the mixture was heated to 90° C. for 4 h. The mixture was poured into 3 M HCl (40 mL) solution and the product was extracted with EtOAc (2×40 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography provided 2,2,2-trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazol-5-ylcarbamate (0.88 g, 80% yield) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ 7.36-7.34 (m, 3H), 7.07 (dd, J=5.6 Hz, 4.0 Hz, 1H), 6.52 (s, 1H), 5.83 (t, J=7.2 Hz, 3H), 4.95 (s, 2H), 4.66-4.62 (m, 1H), 1.45 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 382.0 (M+H+).

후처리

  1. extractionthe product was extracted with EtOAc (2×40 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-c0c9cca43ad8428dbf78179843149592
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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