Imidazole → 3,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one

HRID 904652ノート

反応式

HRID 904652 の反応式
[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5](Br)[O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.O.O.O.O.C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1>C(#N)C>[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1

参加物

5

反応物 3

HCID 795ImidazoleHCID 130194363,3-Bis-fluoromethyl-1-bromo-1-(4-chlorophenoxy)-butan-2-oneHCID 53249422Naphthalene-1,5-disulfonic acid tetrahydrate

生成物 1

HCID 130194373,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

61.5 g (0.18 mol) of 3,3-bis-fluoromethyl-1-bromo-1-(4-chlorophenoxy)-butan-2-one were stirred with 27.2 g (0.4 mol) of imidazole in 500 ml of acetonitrile at 45° C. for 4 hours. The solvent was distilled off under a waterpump vacuum, the oil which remained was taken up in 500 ml of methylene chloride, the organic phase was washed twice with 1,000 ml of water and dried over sodium sulphate and the solvent was distilled off. The oil was taken up in acetone, 36 g (0.1 mol) of 1,5-naphthalenedisulphonic acid tetrahydrate were added and the precipitate formed was filtered off. The precipitate (the 1,5-naphthalenedisulphonate of the compound of Example 3) was treated with sodium bicarbonate solution. 14 g (24% of theory) of 3,3-bis-fluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one were obtained as a viscous oil.

後処理

  1. distillationThe solvent was distilled off under a waterpump vacuum
  2. washthe organic phase was washed twice with 1,000 ml of water
  3. dry with materialdried over sodium sulphate
  4. distillationthe solvent was distilled off
  5. customthe precipitate formed
  6. filtrationwas filtered off
  7. additionThe precipitate (the 1,5-naphthalenedisulphonate of the compound of Example 3) was treated with sodium bicarbonate solution

出典と根拠

ORDレコード
ord-a72aaebd3481469bbbb89412c50d45e5
出典データセット
uspto-grants-1983_12
特許番号
US04419361

反応ノート

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