4-(Bromoacetyl)benzonitrile → HCID 86618619, compound

HRID 1436453Notes

Reaction equation

HRID 1436453 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 86618619HCID 86618619, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-83d592538b454ec19c2c2e0eee164611
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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