Water → HCID 86655660, compound

HRID 2047441Notes

Reaction equation

HRID 2047441 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[CH3:25]I.O>CN(C=O)C>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[C:5]([N:13]([CH3:25])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2224650HCID 2224650, compound

Product 1

HCID 86655660HCID 86655660, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound (12.1 g) obtained in step 1 in DMF (55 mL) was added sodium hydride (1.82 g) at 0° C. The reaction mixture was stirred at 0° C. for 5 min, methyl iodide (11.4 mL) was added dropwise, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water, and extracted twice with ethyl acetate. The extract was washed with saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (10% ethyl acetate/hexane) to give tert-butyl [3,5-bis(trifluoromethyl)phenyl](methyl)carbamate (12.5 g, 99%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionextracted twice with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2655f2eaa3144ec1b0ec101d9a1534be
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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