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

HRID 1975951노트

반응식

HRID 1975951 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3228a6fc3dfd4bff9360a52dee1272ef
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225316B1

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