Triethylamine → HCID 474086、化合物

HRID 1857775ノート

反応式

HRID 1857775 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH3:16])[C:13]([CH2:17][CH2:18][CH2:19][OH:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:26]([N:28]=C=O)=[O:27].C(N(CC)CC)C>O1CCCC1.O>[C:26]([O:20][CH2:19][CH2:18][CH2:17][C:13]1[N:14]([CH2:15][CH3:16])[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:21]([CH3:22])[CH3:23])[N:12]=1)(=[O:27])[NH2:28]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 4740851H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-

生成物 1

HCID 474086HCID 474086、化合物収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

In 7 ml of dry tetrahydrofuran was dissolved 700 mg (1.9 mmol) of the alcohol (137b), and after the solution was cooled to -40° C., 530 mg (2.8 mmol) of trichloroacetyl isocyanate was added, the temperature was elevated to room temperature. After 30 minutes, 2 ml of water and 1 ml of triethylamine were added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 705 mg (yield 90%) of Compound I-149 as crystals. mp 128-129° C.

後処理

  1. customwas elevated to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (3% methanol-ethyl acetate)
  8. customrecrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-303df69df31c4603b0580a23f27c8fb2
出典データセット
uspto-grants-2000_11
特許番号
US06147097

反応ノート

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