4-(Bromoacetyl)benzonitrile → HCID 86618595, compound

HRID 1436390Notes

Reaction equation

HRID 1436390 reaction equation
[OH:1][CH:2]([CH3:10])[C:3]([NH:6][C:7]([NH2:9])=[S:8])([CH3:5])[CH3:4].[Br:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)=O>C(O)C>[BrH:11].[OH:1][CH:2]([CH3:10])[C:3]([NH:6][C:7]1[S:8][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[N:9]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 86618597HCID 86618597, compound

Product 1

HCID 86618595HCID 86618595, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2-hydroxy-1,1-dimethylpropyl)thiourea (720 mg, 4.4 mmol), prepared in the previous step, and 2-bromo-4′-cyano-acetophenone (980 mg, 4.4 mmol) in 20 mL of ethanol was heated under nitrogen to dissolve all of the solids. The reaction was allowed to come to room temperature and then stirred at room temperature overnight. The solid was collected by filtration and dried under reduced pressure to give 4-{2-[(2-hydroxy-1,1-dimethylpropyl)amino]-1,3-thiazol-4-yl}benzonitrile hydrobromide (1.3157 g, 81%) as a white solid, mp 208-210° C.; MS (ES) m/z 286.0 [M−H]−.

Workup

  1. temperaturewas heated under nitrogen
  2. dissolutionto dissolve all of the solids
  3. customto come to room temperature
  4. filtrationThe solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-279b71fa289a456dbbbbadba29bd3d56
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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