Trichloroacetyl chloride → 2,2,2-Trichloro-1-{10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

HRID 639279ノート

反応式

HRID 639279 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[C:4]([CH3:26])[CH:3]=1.C(N(CC)CC)C.[Cl:34][C:35]([Cl:40])([Cl:39])[C:36](Cl)=[O:37]>ClCCl>[Cl:34][C:35]([Cl:40])([Cl:39])[C:36]([C:21]1[N:13]2[C:12]([CH2:11][N:10]([C:8](=[O:9])[CH2:7][O:6][C:5]3[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][C:4]=3[CH3:26])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14]2)=[CH:23][CH:22]=1)=[O:37]

参加物

5

反応物 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 6868101910-[(4-Chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

生成物 1

HCID 160392952,2,2-Trichloro-1-{10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cold (0° C.) solution of 10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of step B (2.70 mmol) and triethylamine (0.76 mL) in dichloromethane (15 mL) was added trichloroacetyl chloride (0.90 mL). This was stirred and allowed to warm to room temperature overnight. The reaction mixture was washed with water (2×), 0.1N hydrochloric acid (2×), dilute aqueous sodium bicarbonate (2×) and finally, with water (1×). The organic phase was dried over anhydrous sodium sulfate and evaporated. The product was purified by crystallization from warm ethyl acetate/hexane (3/1), m.p. 156-158° C. MS [(+)ESI, m/z]: 511 [M+H]+ Anal. Calcd for C23H18Cl4O3: C, 53.93; H, 3.54; N, 5.47. Found: C, 53.90; H, 3.45; N, 5.40.

後処理

  1. washThe reaction mixture was washed with water (2×), 0.1N hydrochloric acid (2×), dilute aqueous sodium bicarbonate (2×)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe product was purified by crystallization
  5. temperaturefrom warm ethyl acetate/hexane (3/1), m.p. 156-158° C

出典と根拠

ORDレコード
ord-6e271626b6294a2b928922a356001741
出典データセット
uspto-grants-2010_04
特許番号
US07691848B2

反応ノート

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