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5,6-Dimethylbenzimidazole → 2-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamate

HRID 724169
ノート
印刷プレビュー

反応式

HRID 724169 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:26][C:27]1[C:35]([CH3:36])=[CH:34][C:30]2[N:31]=[CH:32][NH:33][C:29]=2[CH:28]=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:31]3[C:30]4[CH:34]=[C:35]([CH3:36])[C:27]([CH3:26])=[CH:28][C:29]=4[N:33]=[CH:32]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6755,6-DimethylbenzimidazoleHCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

生成物 1

HCID 213004172-[4-(5,6-Dimethyl-1H-benzimidazol-1-yl)phenyl}ethyl (4-methylphenyl)sulfonylcarbamate収率 22%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate
触媒
HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)oxy]ethyl}phenylboronic acid (100 mg, 0.28 mmol), 5,6-dimethylbenzimidazole (40 mg, 0.28 mmol), Cu(OAc)2 (60 mg, 0.33 mmol), triethylamine (115 μl, 0.83 mmol), MS4A (100 mg), and CH2Cl2 (4 ml) was stirred at room temperature for 1 week. After filtration through a bed of celite, the filtrate was diluted with CH2Cl2, and washed with water. The organic fraction was dried over MgSO4 and filtered. After concentration under reduced pressure, the residue was purified by preparative TLC (CH2Cl2/MeOH=10/1) to afford 28 mg (22%) of the title compound.

後処理

  1. filtrationAfter filtration through a bed of celite
  2. additionthe filtrate was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic fraction was dried over MgSO4
  5. filtrationfiltered
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by preparative TLC (CH2Cl2/MeOH=10/1)

出典と根拠

ORDレコード
ord-8b3d909bc9494d0787c1fff36e4418a8
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141580B2

反応ノート

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