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Methylamine → 6-bromo-N-methyl-2-naphtamide

HRID 724202
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HRID 724202 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.Cl.[CH2:16]([N:18]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.CN>CN(C)C=O.C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:18][CH3:16])=[O:14])[CH:6]=[CH:5]2
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참가 물질

9

반응물 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 45498526-Bromo-2-naphthalenecarboxylic acid

생성물 1

HCID 218796286-bromo-N-methyl-2-naphtamide수율 95.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

6-Bromo-2-naphthoic acid (60.26 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.21 g) and 1-hydroxy-1H-benzotriazole monohydrate (44.1 g) were dissolved in dimethylformamide (960 ml) under an argon atmosphere. N-Ethyldiisopropylamine (37.23 g) was added with stirring under ice-cooling. A solution (2M; 192 ml) of methylamine in THF was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (8 L) with stirring and the precipitate was collected by filtration. The precipitate was washed successively with water and diisopropyl ether, and dried in the presence of phosphorus pentaoxide at 70° C. to give the title compound (60.6 g) as a crystalline powder.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. washThe precipitate was washed successively with water and diisopropyl ether
  6. dry with materialdried in the presence of phosphorus pentaoxide at 70° C.

출처 및 근거

ORD 기록
ord-4d3f1c0be4c248248a53381ce6b49229
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141598B2

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