Hydrochloric Acid → Methyl 4-[methyl(3-phenylpropanoyl)amino]benzoate

HRID 642143

반응식

HRID 642143 반응식
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:13](Cl)(=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.Cl>N1C=CC=CC=1>[CH3:1][N:2]([C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 64801Benzenepropanoyl chlorideHCID 140375Methyl 4-methylaminobenzoate

생성물 1

HCID 9814733Methyl 4-[methyl(3-phenylpropanoyl)amino]benzoate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of methyl 4-methylaminobenzoate (1.0 g, 6.05 mmol) in anhydrous pyridine (20 mL) was added dropwise hydrocinnamoyl chloride (1080 μL) at rt. After 16 hrs water (5 mL) was added and the resulting mixture was stirred for 1 hr at rt. The resulting mixture was poured into water (300 mL) and HCl (5 N, 50 mL) was added. The compound was extracted with AcOEt (2×300 mL) and washed with a saturated aqueous solution of NaHCO3 (150 mL). The combined organic layers were dried over MgSO4 and evaporated under vacuo to give the title compound (1.80 g) was obtained as a beige solid (95%) in 95.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

후처리

  1. additionwas added
  2. extractionThe compound was extracted with AcOEt (2×300 mL)
  3. washwashed with a saturated aqueous solution of NaHCO3 (150 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated under vacuo

출처 및 근거

ORD 기록
ord-0f3b38928b8044e5bcb67e914b504343
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696231B2

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