1,2-Dichloroethane → Phenylmethyl 3-amino-4-methoxybenzoate

HRID 1776539노트

반응식

HRID 1776539 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[C:13]1([CH2:19]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6]

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 178233-Amino-4-methoxybenzoic acid

생성물 1

HCID 54195745Phenylmethyl 3-amino-4-methoxybenzoate수율 52%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

3-amino-4-methoxybenzoic acid (20 g, 120 mmol), phenylmethanol (12.94 g, 120 mmol), DMAP (14.62 g, 120 mmol), and EDC (22.94 g, 120 mmol) were dissolved in DMF (100 ml). The reaction was stirred at RT for 2 hours. The reaction mixture was filtered, and the mother liquor was diluted with water and extracted with EtOAc. The organic phase was extracted with water, dried over Na2SO4 and evaporated under vacuum. The crude product was crystallized in EtOAc. The mother liquor are purified by flash chromatography (Petroleum Ether/EtOAc 80/20). The overall amount of the desired product was 16 g (Yield: 52%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. additionthe mother liquor was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic phase was extracted with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum
  7. customThe crude product was crystallized in EtOAc
  8. customThe mother liquor are purified by flash chromatography (Petroleum Ether/EtOAc 80/20)

출처 및 근거

ORD 기록
ord-99caeb0deeeb494fa8916ecc0d29ad34
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

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