Ethyl Acetate → 1-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea

HRID 2278947노트

반응식

HRID 2278947 반응식
Cl.[F:2][C:3]([F:9])([F:8])[O:4][CH2:5][CH2:6][NH2:7].[H-].[Na+].[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].CCOC(C)=O>C1COCC1>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:7][CH2:6][CH2:5][O:4][C:3]([F:9])([F:8])[F:2])=[O:17]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 448908072-(Trifluoromethoxy)ethan-1-amine hydrochloride

생성물 1

HCID 904257591-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea수율 140%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A 0° C. suspension of 2-(trifluoromethoxy)ethylamine hydrochloride (0.308 g, 1.861 mmol) in THF (10 mL) was treated with NaH (60% in mineral oil, 0.082 g, 2.047 mmol), stirred at 0° C. for 0.5 h, treated drop-wise with 2-chloroethyl isocyanate (0.175 mL, 2.047 mmol), allowed to warm to RT and stirred overnight. The mixture was treated with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness to afford 1-(2-chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea (610 mg, 140%) containing EtOAc. 1H NMR (400 MHz, DMSO-d6): δ 6.29 (br s, 2 H), 4.04-3.97 (m, 2 H), 3.55 (t, J=6.2 Hz, 2 H), 3.33-3.24 (m, 4 H).

후처리

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customthe solids removed via filtration
  4. concentrationthe filtrate concentrated to dryness

출처 및 근거

ORD 기록
ord-6c489c2a969341599c02bd99165fbf6a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133183B2

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