Potassium Carbonate → 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide

HRID 660058ノート

反応式

HRID 660058 の反応式
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:22]=[CH:21][CH:20]=[CH:19][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:11].Br[CH2:24][CH2:25][S:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)(=O)C.CCCCCC>CN(C=O)C.C(OCC)(=O)C.O>[CH:27]1([S:26][CH2:25][CH2:24][S:7][C:8]2[N:22]=[CH:21][CH:20]=[CH:19][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22455667((2-Bromoethyl)thio)cyclohexaneHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

生成物 1

HCID 252216282-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide収率 34%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

607 mg (4.4 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide (V1) in DMF (5 ml), and the mixture was stirred for 1 h at RT. 446 mg of (2-bromoethyl)-(cyclohexyl)sulfane (crude product V2) were then added, and stirring was continued for a further 18 h at RT. The mixture was then diluted with ethyl acetate, and water was added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. CC (ethyl acetate/n-hexane 1:1) with the residue yielded 268 mg (0.68 mmol, 34%) of 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide. MS: m/z 393.1 [M+H]+.

後処理

  1. stirringstirring
  2. waitwas continued for a further 18 h at RT
  3. additionwas added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-94ddc86d71c64fd888d40ac1c2768cdd
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

反応ノート

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