Methylamine → N-Methyl-[2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetamide

HRID 1200189노트

반응식

HRID 1200189 반응식
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=O)=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:22]([N:24](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN>ClCCl>[CH3:22][NH:24][C:19](=[O:21])[CH2:18][C:17]1[C:9]2[O:8][C:7]([C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=3)=[CH:12][C:11](=[O:13])[C:10]=2[CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 14650449HCID 14650449, 화합물

생성물 1

HCID 14650457N-Methyl-[2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (568 mg) and triethylamine (0.34 ml) were added to dichloromethane (6 ml) and to the mixture was added dropwise diphenylphosphoryl azide (0.52 ml) with stirring at room temperature. After stirring for 30 minutes, 30% aqueous methylamine solution (5 ml) was added and stirring was continued for additional 2 hours. The solvent was distilled off under reduced pressure and n-hexane was added to the residue. Crystals deposited were filtered. The crude crystals were recrystallized from methanol to obtain the title compound as prisms, yield 380 mg (64%), m.p. 213°-214° C.

후처리

  1. stirringAfter stirring for 30 minutes
  2. stirringstirring
  3. distillationThe solvent was distilled off under reduced pressure and n-hexane
  4. additionwas added to the residue
  5. filtrationCrystals deposited were filtered
  6. customThe crude crystals were recrystallized from methanol

출처 및 근거

ORD 기록
ord-d3bf68338ce34608b37aa22bb812ae78
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904690

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