4-(Bromoacetyl)benzonitrile → HCID 86618619、化合物

HRID 1436453ノート

反応式

HRID 1436453 の反応式
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[OH:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[S:18]>C(O)C>[OH:13][CH2:14][CH2:15][NH:16][C:17]1[S:18][CH:2]=[C:3]([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[N:19]=1

参加物

4

反応物 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 3254090(2-hydroxyethyl)thiourea

生成物 1

HCID 86618619HCID 86618619、化合物収率 39%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In the same manner as described in step 3 of Example 81, a solution of 4-(2-bromo-acetyl)-benzonitrile (3.8 g, 17.1 mmol) and (2-hydroxy-ethyl)-thiourea, prepared in the previous step, in 50 mL of ethanol was heated at reflux for 2 h. The reaction was concentrated to a residue. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 6.2 g of crude product. The crude product was purified on silica gel using a stepwise gradient of 3:1 to 2:1 hexane:ethyl acetate to give 4-{2-[(2-hydroxyethyl)amino]-1,3-thiazol-4-yl}benzonitrile (1.6 g, 39%), mp 80-82° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction was concentrated to a residue
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated NaHCO3
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give 6.2 g of crude product
  10. customThe crude product was purified on silica gel using a stepwise gradient of 3:1 to 2:1 hexane

出典と根拠

ORDレコード
ord-83d592538b454ec19c2c2e0eee164611
出典データセット
uspto-grants-2009_11
特許番号
US07618990B2

反応ノート

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