4-Chloroaniline → 1-(4-Chlorophenyl)-3-[1-(3-isopropenylphenyl)-1-methyl-ethyl]urea

HRID 64222

반응식

HRID 64222 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[C:7]([N:10]=[C:11]=[O:12])([CH3:9])[CH3:8])([CH3:3])=[CH2:2].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>ClCCl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:11]([NH:10][C:7]([C:6]2[CH:13]=[CH:14][CH:15]=[C:4]([C:1]([CH3:3])=[CH2:2])[CH:5]=2)([CH3:9])[CH3:8])=[O:12])=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 78124-ChloroanilineHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

생성물 1

HCID 191683531-(4-Chlorophenyl)-3-[1-(3-isopropenylphenyl)-1-methyl-ethyl]urea수율 110.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-isopropenyl α, α-dimethylbenzyl isocyanate 2 (473 mg, 2.35 mmol) in dichloromethane (6 mL) at 0° C. was added 4-chloroaniline (300 mg, 2.35 mmol) in dichloromethane (3 mL). The reaction was stirred until complete consumption of starting materials. The precipitated product was collected by filtration and washed with dichloromethane to give 5b (852 mg, 80%). mp 234-236° C. Yield 80%; 1H NMR (DMSO-d6, 400 MHz) δ 1.58 (s, 6H), 2.08 (s, 3H), 5.06 (s, 1H), 5.36 (s, 1H), 6.64 (s, 1H), 7.20 (d, J=6.4 Hz, 2H), 7.23-7.32 (m, 5H), 7.47 (s, 1H), 8.55 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 22.24, 30.30, 55.0, 113.06, 119.50, 122.35, 123.69, 124.86, 124.95, 128.65, 129.09, 140.11, 140.73, 143.60, 148.95, 154.53; ESI-HRMS for C9H22N2OCl (M+H)+ calcd. 329.1421. found 329.1418.

후처리

  1. filtrationThe precipitated product was collected by filtration
  2. washwashed with dichloromethane

출처 및 근거

ORD 기록
ord-130c08263bab4fa8a36c2aa83743a947
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447134B2

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