Hydrochloric Acid → HCID 22327356, compound

HRID 495655Notes

Reaction equation

HRID 495655 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[N:13]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:14](=O)[O:15]CC.[H-].[Na+].Cl>C(O)C>[Br:8][C:6]1[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:3]2[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[CH:21]=3)[C:14](=[O:15])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 22327386Ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate

Product 1

HCID 22327356HCID 22327356, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl[3-(trifluoromethyl)benzyl]carbamate (257.8 mg) in ethanol (10 ml) was added sodium hydride (60%) (48.7 mg). The reaction mixture was heated at reflux for 1.5 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (247.7 mg, quantitative yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87fae63e2f684a53be773234a6ad73ae
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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