Chloroacetonitrile → HCID 14349018、化合物

HRID 2107700ノート

反応式

HRID 2107700 の反応式
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.Cl[CH2:30][C:31]#[N:32].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:31]([CH2:30][N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1)#[N:32]

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 14348987HCID 14348987、化合物

生成物 1

HCID 14349018HCID 14349018、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (16 g, 0.052 mole), chloroacetonitrile (8 g, 0.10 mole) and sodium bicarbonate (17 g, 0.20 mole) in DMF (125 ml) was warmed at 70° C. for 2.5 hours. The mixture was concentrated to an oil which was stirred with water and extracted with ethyl acetate. The organic extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil (18 g) which solidified upon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C.). A sample was recrystallized from hexanes to yield 3-cyanomethyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, m.p. 134°-135° C.

後処理

  1. concentrationThe mixture was concentrated to an oil which
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed twice with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent was evaporated to an oil (18 g) which
  7. customupon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C.)
  8. customA sample was recrystallized from hexanes

出典と根拠

ORDレコード
ord-7348cb5fd59047a787ece2e68fdace77
出典データセット
uspto-grants-1990_06
特許番号
US04935418

反応ノート

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