Water → Dimethyl 2-(4-chlorobenzoylamino)malonate

HRID 2251708노트

반응식

HRID 2251708 반응식
Cl.[NH2:2][CH:3]([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.O>ClCCl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:2][CH:3]([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])=[O:18])=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 2734846Dimethyl 2-aminomalonate hydrochloride

생성물 1

HCID 68614697Dimethyl 2-(4-chlorobenzoylamino)malonate수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Part A: To a stirred solution of dimethyl aminomalonate hydrochloride (25 gram, 0.136 mol) in dichloromethane (200 mL) triethylamine (41.4 mL, 2.2 molar equivalent) is added at 0° C. 4-Chlorobenzoyl chloride (23.8 gram, 0.136 mol) is slowly added and the resulting solution is allowed to stand at room temperature overnight. Water is added and the organic layer is separated. The water layer is extracted twice with dichloromethane. The collected organic layers are washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue is recrystallised from methanol (400 mL) to give dimethyl 2-(4-chlorobenzoylamino)malonate (30.5 gram, 79% yield). Melting point: 146-148° C. 1H-NMR (200 MHz, CDCl3): δ 3.86 (s, 6H), 5.38 (d, J=6 Hz, 1H), 7.15 (br d, J˜6 Hz, 1H), 7.43 (d, J=8 Hz, 2H), 7.79 (d, J=8 Hz, 2H).

후처리

  1. customthe organic layer is separated
  2. extractionThe water layer is extracted twice with dichloromethane
  3. washThe collected organic layers are washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallised from methanol (400 mL)

출처 및 근거

ORD 기록
ord-32fa02d866454be2ad382e22270dd4b4
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319110B2

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