Sodium Chloride → alpha-(p-Bromophenyl)-alpha-phenyl-1-(toluene-p-sulphonyl)imidazole-2-methanol

HRID 261930

反応式

HRID 261930 の反応式
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[Br:27][C:28]1[CH:41]=[CH:40][C:31]([C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])=[CH:30][CH:29]=1.[Cl-].[Na+]>C(OCC)C.O1CCCC1>[Br:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:11]2[N:10]([S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:15])=[CH:6][CH:5]=3)(=[O:8])=[O:9])[CH:14]=[CH:13][N:12]=2)[OH:33])=[CH:40][CH:41]=1

参加物

8

反応物 5

HCID 5234Sodium ChlorideHCID 70304-BromobenzophenoneHCID 8058HexaneHCID 752191-(p-Toluenesulfonyl)imidazoleHCID 178418339Butyllithium

生成物 1

HCID 11838798alpha-(p-Bromophenyl)-alpha-phenyl-1-(toluene-p-sulphonyl)imidazole-2-methanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 33.3 g. (0.15 mol) of 1-(toluene-p-sulphonyl)imidazole (H. A. Staab and K. Wendel, Ber. 93, (1960) 2902) in 300 ml. of anhydrous tetrahydrofuran and 150 ml. of anhydrous diethyl ether at a temperature of -40° to -50° C. under a nitrogen atmosphere were added drop-wise 91 ml. of a 20% solution of butyllithium in n-hexane (0.20 mol.) dissolved in 150 ml. of anhydrous diethyl ether. Upon completion of the addition, the mixture was kept at a temperature of -40° to -50° C. for one hour. Next and under identical conditions as to temperature 44.4 g. (0.17 mol) of 4-bromobenzophenone in 200 ml. of anhydrous tetrahydrofuran and 100 ml. of anhydrous diethyl ether were added drop-wise and the mixture was kept under the same conditions for another 3.5 hours. Cooling was stopped and the mixture was allowed to reach ambient temperature in 1/2 hour. It was then poured out into about 250 ml. of a sodium chloride solution. The aqueous layer was separated and discarded, the organic solvents layer was washed with 100 ml. of a sodium chloride solution, dried and concentrated. The residual oil was brought to crystallisation by addition of a very small amount of diethyl ether. Purification was brought about by crystallisation from warm ethanol to which some acetone was added. Melting point of the product was 138°-140° C.

後処理

  1. additionUpon completion of the addition
  2. waitthe mixture was kept under the same conditions for another 3.5 hours
  3. temperatureCooling
  4. waitto reach ambient temperature in 1/2 hour
  5. additionIt was then poured out into about 250 ml
  6. customThe aqueous layer was separated
  7. washthe organic solvents layer was washed with 100 ml
  8. dry with materialof a sodium chloride solution, dried
  9. concentrationconcentrated
  10. customThe residual oil was brought to crystallisation by addition of a very small amount of diethyl ether
  11. customPurification
  12. customwas brought about by crystallisation
  13. temperaturefrom warm ethanol to which some acetone
  14. additionwas added
  15. customwas 138°-140° C.

出典と根拠

ORDレコード
ord-3e1834d297294bc393470161d924428f
出典データセット
uspto-grants-1979_05
特許番号
US04152441

関連ノート

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