Triethylamine → Diethyl p-toluoylaminomalonate

HRID 263977

반응식

HRID 263977 반응식
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:21]1([CH3:30])[CH:26]=[CH:25][C:24]([C:27](Cl)=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:30][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:28])=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

생성물 1

HCID 17447783Diethyl p-toluoylaminomalonate수율 94.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of diethyl aminomalonate hydrochloride (20.95 g, 97.02 mmol) and dry CH2Cl2 (180 mL) was added triethylamine (29.7 mL, 213 mmol). After cooling to 0° C., a solution of p-toluoyl chloride (15 g, 97 mmol) and CH2Cl2 (25 mL) was added at a rate such that the reaction temperature remained less than 5° C. The reaction was stirred at room temperature for 1 hour, cooled to 0° C. and quenched with water (90 mL). The organic layer was separated and washed with water (2×100 mL), 10% HCl (2×100 mL), water (2×100 mL) and brine (100 mL). The resultant solution was dried (Na2SO4), filtered and concentrated to give the title compound (26.8 g, 94%) as a white solid: mp 98°-99° C.

후처리

  1. customremained less than 5° C
  2. temperaturecooled to 0° C.
  3. customquenched with water (90 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×100 mL), 10% HCl (2×100 mL), water (2×100 mL) and brine (100 mL)
  6. dry with materialThe resultant solution was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-257568f684614d14905001349cf072f5
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646168

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