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

HRID 1993745Notes

Reaction equation

HRID 1993745 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 6. 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 3, 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-08fdf228e0854dab82b05a3d62b1891a
Source dataset
uspto-grants-2010_01
Patent number
US07652018B2

Reaction notes

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