Methyl chloroformate → 2-Amino-3-(2-methyl-6-methoxycarbonylaminobenzylideneamino)pyridine

HRID 2073802

반응식

HRID 2073802 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]([O:21][CH3:22])=[O:20])[C:11]=1[CH:12]=O.CC1C=CC=C(N)C=1C=O.ClC(OC)=O>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.O.C(N(CC)CC)C>[NH2:1][C:2]1[C:7]([N:8]=[CH:12][C:11]2[C:14]([NH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=[CH:17][C:10]=2[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

9

반응물 4

HCID 6586Methyl chloroformateHCID 99562,3-DiaminopyridineHCID 144998232-Methyl-6-methoxycarbonylaminobenzaldehydeHCID 230465382-Amino-6-methylbenzaldehyde

생성물 1

HCID 144998242-Amino-3-(2-methyl-6-methoxycarbonylaminobenzylideneamino)pyridine수율 19.6%

시약·촉매·용매 4

HCID 24193Titanium Tetrachloride촉매HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

To a solution of 2,3-diaminopyridine (546 mg) and 2-methyl-6-methoxycarbonylaminobenzaldehyde (966 mg)*, which was prepared by reacting 2-methyl-6-aminobenzaldehyde with methyl chloroformate according to a similar manner to that of Preparation 2, and triethylamine (2.5 g) in methylene chloride (26 ml) was added a 0.5M solution of titanium tetrachloride in methylene chloride (6 ml) at 0° C. and the mixture was stirred for 2 hours at the same temperature. To the mixture, water was added and the insoluble materials were removed by filtration, and the organic layer was separated. The solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (27 g), eluting with a mixture of chloroform and methanol (50:1). The fractions containing the desired product were combined and the solvent was removed under reduced pressure. The residue was triturated with diethyl ether to give 2-amino-3-(2-methyl-6-methoxycarbonylaminobenzylideneamino)pyridine (279 mg).

후처리

  1. customthe insoluble materials were removed by filtration
  2. customthe organic layer was separated
  3. customThe solvent was evaporated under reduced pressure
  4. washeluting with a mixture of chloroform and methanol (50:1)
  5. additionThe fractions containing the desired product
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-0170d304173d4fbaaa3ebafe0360ad10
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04920129

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