4-(Bromoacetyl)benzonitrile → HCID 86618619, 화합물

HRID 1436453노트

반응식

HRID 1436453 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 86618619HCID 86618619, 화합물수율 39%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83d592538b454ec19c2c2e0eee164611
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618990B2

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