Sodium hydride → HCID 4164583, compound

HRID 1091328Notes

Reaction equation

HRID 1091328 reaction equation
ClC1C=C(N)C=CC=1C.[C:10]1([O:16][C:17](=[O:27])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([Cl:26])[CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Na+]>C1COCC1>[C:10]1([O:16][C:17](=[O:27])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([Cl:26])[CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66589676HCID 66589676, compound

Product 1

HCID 4164583HCID 4164583, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of (3-chloro-4-methyl-phenyl)-carbamic acid phenyl ester 2-chloro-4-amino toluene (282 mg, 2 mmol) was dissolved in THF (10 mL). The mixture was added sodium hydride (128 mg, 3.2 mmol) and stirred at room temperature for 15 minutes. Diphenyl N-cyano-carbonimidate (715 mg, 3.0 mmol) was added and the mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature, quenched by saturated NH4Cl (10 mL), filtered and the solid was dried in oven to give (3-chloro-4-methyl-phenyl)-carbamic acid phenyl ester as solid (0.5 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched by saturated NH4Cl (10 mL)
  5. filtrationfiltered
  6. customthe solid was dried in oven

Sources & evidence

ORD record
ord-617e6099e49240f29dde1946789659f4
Source dataset
uspto-grants-2012_03
Patent number
US08129375B2

Reaction notes

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