Trichloroacetyl isocyanate → [4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methyl carbamate

HRID 353075노트

반응식

HRID 353075 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]([CH2:13][OH:14])[C:10]=1[CH2:11][CH3:12].ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24]>ClCCl>[C:23](=[O:24])([O:14][CH2:13][N:9]1[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][C:4]2[CH:17]=[C:18]([Cl:20])[CH:19]=[C:2]([Cl:1])[CH:3]=2)[C:7]([CH2:15][CH3:16])=[N:8]1)[NH2:25]

참가 물질

4

반응물 2

HCID 76400Trichloroacetyl isocyanateHCID 9857970[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methanol

생성물 1

HCID 10269633[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methyl carbamate수율 74.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of the alcohol of Example 41 (280 mg, 0.90 mmol) in dichloromethane (5 ml) was cooled to 0° C., treated with trichloroacetyl isocyanate (128 l, 1.1 mmol) and stirred at 0° C. for 30 minutes. The solution was soaked into a pad of alumina (neutral, activity II, Brockmann), washed with dichloromethane and then extracted with ethyl acetate. The organic extract was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (2:1, by volume) gradually changing to cyclohexane:ethyl acetate (1:1, by volume) to afford the title compound (238 mg) as a solid, m.p. 153-155° C.

후처리

  1. washwashed with dichloromethane
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (2:1, by volume)

출처 및 근거

ORD 기록
ord-67f19ec7f553418b813f991a1a3f3459
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750230B2

반응 노트

불러오는 중…