1,2-Dichloroethane → HCID 22328602, 화합물

HRID 586130

반응식

HRID 586130 반응식
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:15]=1[C:16](O)=[O:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:16](=[O:17])[C:15]1[C:14]([OH:13])=[CH:22][CH:21]=[CH:20][C:19]=1[OH:23])[CH3:2]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 93382,6-Dihydroxybenzoic AcidHCID 181649HOAtHCID 296018Benzenemethanamine, N-ethyl-4-methoxy-

생성물 1

HCID 22328602HCID 22328602, 화합물수율 32.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of N-ethyl-4-methoxybenzyl amine (1.07 g, 6.49 mmol) in DMF (10 mL) was added 2,6-dihydroxybenzoic acid (1.0 g, 6.49 mmol) followed by HOAt (0.97 g, 7.14 mmol) and EDC (1.31 g, 6.81 mmol). After stirring overnight, the reaction was diluted with EtOAc prior to washing 3× with H2O. The combined aqueous layers were extracted once with EtOAc. The organic fractions were combined, washed once with brine, and dried over Na2SO4 prior to concentrating using a rotary evaporator. The residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent. The resulting promising impure fractions were further purified by silica gel chromatography. A total of 631 mg of the desired N-ethyl-N-4-methoxybenzyl 2,6-dihydroxybenzamide was obtained.

후처리

  1. washto washing 3× with H2O
  2. extractionThe combined aqueous layers were extracted once with EtOAc
  3. washwashed once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationto concentrating
  6. customa rotary evaporator
  7. customThe residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent
  8. customThe resulting promising impure fractions were further purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-5e527322bbd34ff1bd7734ab74b1d29f
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936590B2

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