Water → N-(3,5-bis(trifluoromethyl)benzyl)-N-methyl-3-o-tolylisonicotinamide

HRID 1975951ノート

反応式

HRID 1975951 の反応式
[CH3:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:33]Br.O>O1CCCC1>[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:33][N:2]([CH3:1])[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

参加物

6

反応物 4

HCID 962WaterHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22000076n-Methyl-3-o-tolyl-isonicotinamide

生成物 1

HCID 9846661N-(3,5-bis(trifluoromethyl)benzyl)-N-methyl-3-o-tolylisonicotinamide収率 97.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 226 mg (1 mmol) N-methyl-3-o-tolyl-isonicotinamide in 10 ml tetrahydrofuran were added dropwise 1.3 ml (1.3 mmol) 1M potassium hexamethyldisilazide solution in tetrahydrofuran at room temperature. The white suspension was stirred for 30 min at room temperature and 0.18 ml (1 mmol) 3,5-bis(trifluoromethyl)benzyl bromide were added at the same temperature. The light brown suspension was stirred for 1 h and water was added. The aqueous layer was separated and washed with ethyl acetate. The combined organic layers were washed twice with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 440 mg (97%) of the title compound as a light brown oil.

後処理

  1. stirringThe light brown suspension was stirred for 1 h
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. washThe combined organic layers were washed twice with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

出典と根拠

ORDレコード
ord-3228a6fc3dfd4bff9360a52dee1272ef
出典データセット
uspto-grants-2001_05
特許番号
US06225316B1

反応ノート

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