Dimethylformamide → Methyl 4-(4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylate

HRID 2079830ノート

反応式

HRID 2079830 の反応式
[CH3:1][NH:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]([O:15][CH3:16])=[O:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=O.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[F:28][C:29]([F:42])([F:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1NN=[N:38][N:37]=1>C(Cl)Cl>[CH3:1][N:2]1[C:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([F:28])([F:42])[F:41])=[N:37][N:38]=[C:3]1[C:5]12[CH2:12][CH2:11][C:8]([C:13]([O:15][CH3:16])=[O:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22591692HCID 22591692、化合物HCID 178506136HCID 178506136、化合物

生成物 1

HCID 20755116Methyl 4-(4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Carboxylate 1-B (2.76 g, 12.3 mmol) was dissolved in methylene chloride (100 ml). Oxalyl chloride (2.0 M, 15.3 ml) was added to the resulting solution followed by DMF (0.19 ml, 2.45 mmol). The reaction mixture was then stirred at room temperature under a nitrogen atmosphere for 2 hours before it was concentrated and stripped from toluene 3 times. The residue was redissolved in toluene (100 ml), treated with 5-[2-(trifluoromethyl)phenyl]-1H-tetrazole (3.15 g, 14.7 mmol) and heated at 100° C. under nitrogen for 12 hours. The product, 1,2,4-triazole 1-C, which precipitated out of reaction mixture as the HCl salt, was dissolved in methylene chloride, washed twice with saturated aqueous sodium bicarbonate solution, dried (MgSO4) and stripped to yield 1-C as a white solid. MS (ESI+)=394.2 (M+1); 1H NMR (500 MHz, CDCl3): δ 2.00 (6H, m), 2.18 (6H, m), 3.48 (3H, s), 3.72 (3H, s), 7.51 (1H, m), 7.71 (2H, m), 7.85 (1H, m) ppm.

後処理

  1. concentrationwas concentrated
  2. dissolutionThe residue was redissolved in toluene (100 ml)
  3. temperatureheated at 100° C. under nitrogen for 12 hours
  4. customThe product, 1,2,4-triazole 1-C, which precipitated out of reaction mixture as the HCl salt
  5. dissolutionwas dissolved in methylene chloride
  6. washwashed twice with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-a856bdc3c1ba418ab2d7f156f2b38b0e
出典データセット
uspto-grants-2011_04
特許番号
US07932280B2

反応ノート

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