Acetic Acid → 1-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

HRID 499939노트

반응식

HRID 499939 반응식
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[CH2:15][NH2:16].[O-:19][C:20]#[N:21].[K+].C(O)(=O)C>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:6]=1[CH2:15][NH:16][C:20]([NH2:21])=[O:19]

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 44235013(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)phenyl)methanamine

생성물 1

HCID 442352571-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Example 1B (9.0 g, 35 mmol), potassium cyanate (4.2 g, 52 mmol), and glacial acetic acid (3.1 mL, 52 mmol) in THF (70 mL) and water (7 mL) was stirred at 60° C. for 2 hours, diluted with ethyl acetate, and sequentially washed with saturated aqueous NaHCO3 and brine. The organic layer was concentrated under reduced pressure to provide the title compound. 1H-NMR (DMSO-d6) δ 7.41 (m, 3H), 4.69 (brs, 1H), 4.45 (d, 2H), 4.37 (brs, 2H), 2.64 (ddd, 2H), 1.45 (ddd, 2H), 0.99 (s, 9H).

후처리

  1. washsequentially washed with saturated aqueous NaHCO3 and brine
  2. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4aba15091225447dad193c4ab4a5006c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767705B2

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