Sodium Bicarbonate → HCID 9842936、化合物

HRID 1166402ノート

反応式

HRID 1166402 の反応式
CC1[N:3]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([C:22]([F:25])([F:24])[F:23])[N:19]=[C:18]3[C:26]3[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])C(C)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:32][C:27]1[C:26]([C:18]2[N:17]([C:14]3[CH:15]=[CH:16][C:11]([S:8]([NH2:3])(=[O:10])=[O:9])=[CH:12][CH:13]=3)[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[N:19]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 22997798HCID 22997798、化合物

生成物 1

HCID 9842936HCID 9842936、化合物収率 78.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6422Trifluoroacetic acid溶媒

実験手順

A mixture of 3-[1-[4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]phenyl]-4,5-dihydro-4-(trifluoromethyl)-1H-imidazol-2-yl]-2-methylpyridine (Step 4) (4.6 g, 0.01 mol) in 75 mL of TFA and 25 mL of water was heated at reflux for 2 hours. The solution was cooled, treated with 400 mL of water and basified with sodium bicarbonate to pH 8. The aqueous phase was extracted with ethyl acetate (400 mL). The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to afford 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a white solid (3.0 g, 78%): mp (DSC): 235-237° C. Anal. Calc'd. for C16H13F3N3O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H,3.29; N, 14.4; S, 8.52.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. extractionThe aqueous phase was extracted with ethyl acetate (400 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

出典と根拠

ORDレコード
ord-baa3ebc49bfd4b6faf8ede6b7f40570a
出典データセット
uspto-grants-2003_09
特許番号
US06613789B2

反応ノート

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