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Sodium Chloride → HCID 18753182、化合物

HRID 1838114
ノート
印刷プレビュー

反応式

HRID 1838114 の反応式
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9]/[C:8](=[CH:11]/[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)/[CH:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:3].C1CCC(N=C=NC2CCCCC2)CC1.O[CH:45]1[CH2:50][C:49](=O)[NH:48][C:46]1=O.C(NCC)C.[Cl-].[Na+]>CN(C)C=O>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9]/[C:8](=[CH:11]/[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([N:48]([CH2:49][CH3:50])[CH2:46][CH3:45])=[O:17])/[CH:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 8021DiethylamineHCID 10868DicyclohexylcarbodiimideHCID 15541115HCID 15541115、化合物HCID 181836963-Hydroxypyrrolidine-2,5-dione

生成物 1

HCID 18753182HCID 18753182、化合物収率 42.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

1.8 g of the Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-benzoic acid base prepared according to example 4 were dissolved in 50 ml analytical grade dimethylformamide, and 2 g DCC and 1.1 g hydroxysuccinimide were added at 0° C. to 15° C. The mixture was stirred at 0° C. for one hour and 2 ml diethylamine were then added dropwise at this temperature. The mixture was stirred at 0° C. for an additional hour and then at room temperature for four days. The reaction mixture was poured on to 300 ml saturated sodium chloride solution and the mixture was then extracted 3 times with 250 ml ethyl acetate each time. The organic phases were washed with 50 ml saturated sodium chloride solution and then dried over magnesium sulfate. The solvent was removed in vacuo. The residue was chromatographed on silica gel with ethyl acetate/methanol=6/5. 0.87 g Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-N,N-diethyl-benzamide base was obtained in this way in the form of an orange-yellow oil. To liberate the hydrochloride, the oil was dissolved in 5 ml acetone, and an equimolar amount of trimethylchlorosilane and water was added. 0.52 g (22.1% of theory) of the title compound 34 was obtained in this way in the form of white crystals.

後処理

  1. additionwere added at 0° C. to 15° C
  2. stirringThe mixture was stirred at 0° C. for an additional hour
  3. waitat room temperature for four days
  4. extractionthe mixture was then extracted 3 times with 250 ml ethyl acetate each time
  5. washThe organic phases were washed with 50 ml saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel with ethyl acetate/methanol=6/5

出典と根拠

ORDレコード
ord-1b183fac29834650bc5e4f50b8855a72
出典データセット
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06673794B2

反応ノート

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