4-(Bromoacetyl)benzonitrile → 4-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

HRID 1436422Notes

Reaction equation

HRID 1436422 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][C:15]([NH:18][C:19]([NH2:21])=[S:20])([CH3:17])[CH3:16]>C(O)C>[OH:13][CH2:14][C:15]([NH:18][C:19]1[S:20][CH:2]=[C:3]([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[N:21]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 22768414N-(1-Hydroxy-2-methylpropan-2-yl)thiourea

Product 1

HCID 866185984-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared in the same manner as described in step 3 of Example 81. 4-(2-bromoacetyl)benzonitrile (1.7 g, 7.4 mmol) and N-(2-hydroxy-1,1-dimethylethyl)thiourea (1.1 g, 7.4 mmol), prepared in step 2 of Example 52, were heated to reflux in 45 mL of ethanol for 30 min. The reaction mixture was cooled to room temperature and the crude product was collected by suction filtration to give 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (2.0 g, 100%), MS (ES) m/z 274 [M+H]+. No further purification was performed on this compound.

Workup

  1. customThis compound was prepared in the same manner
  2. temperaturewere heated
  3. filtrationthe crude product was collected by suction filtration

Sources & evidence

ORD record
ord-20d1ae95970b4f6a9940e23334d58b1c
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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