Acetic Acid → 6-Methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester

HRID 259249ノート

反応式

HRID 259249 の反応式
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][SH:9].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([N+]([O-])=O)=[C:21]([CH3:28])[N:20]=1)=[O:18].C(O)(=O)C>CN(C)C=O>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([C:4]([F:13])([F:14])[F:3])[CH:6]=2)=[C:21]([CH3:28])[N:20]=1)=[O:18]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 1412363-(Trifluoromethyl)benzyl mercaptanHCID 11839201Methyl 6-methyl-5-nitropicolinate

生成物 1

HCID 543879406-Methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To the stirred suspension of 1.08 g of sodium hydride in 25 ml of dimethylformamide the solution of 9.0 g of m-trifluoromethylbenzylmercaptan in 50 ml of dimethylformamide is added during 3 minutes and the mixture stirred for 10 minutes. It is combined with 7.75 g of 6-methyl-5-nitropyridine-2-carboxylic acid methyl ester and the whole stirred on the steam bath for 30 minutes and allowed to stand overnight at room temperature. 2 ml of acetic acid are added and the solution is mixed with ice water to produce a dense, grainy precipitate. It is filtered off and recrystallized from isopropanol-diethyl ether, to yield the 6-methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester melting at 91°-93°.

後処理

  1. additionis added during 3 minutes
  2. stirringthe whole stirred on the steam bath for 30 minutes
  3. waitto stand overnight at room temperature
  4. customto produce a dense, grainy precipitate
  5. filtrationIt is filtered off
  6. customrecrystallized from isopropanol-diethyl ether

出典と根拠

ORDレコード
ord-b557d90e02e242649dbc071b29c93e87
出典データセット
uspto-grants-1977_07
特許番号
US04036965

反応ノート

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