Triethylamine → methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetate

HRID 354376

반응식

HRID 354376 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[Cl:13].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].CCN(CC)CC>C1COCC1>[Cl:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14])=[O:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 76833Chlorophenyl isocyanate2회HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

생성물 1

HCID 23512406methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetate수율 76.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) in THF (20 ml) was added Et3N (0.14 ml, 1.00 mmol) at room temperature. After 1 day stirring, 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) was added to the reaction mixture and stirred 17 h. The reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 3-chloro-4-[N′-(2-chlorophenyl)ureido]phenylacetate (1.35 g, 76%) as a colorless powder. 1H-NMR (CDCl3) δ3.58 (s, 3H), 3.71 (s, 2H), 7.04 (m, 3H), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 7.27-7.39 (m, 3H), 8.07 (m, 2H); MS (ESI) m/z 353 (M++1), 355 (M++3), 357 (M++5).

후처리

  1. stirringstirred 17 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was triturated by the addition of n-hexane

출처 및 근거

ORD 기록
ord-c097c8b9b35247f399ba14bf72666327
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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