Water → HCID 58167761, compound

HRID 39432Notes

Reaction equation

HRID 39432 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][O:8][C:9]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([O:22][CH3:23])[C:10]=1[C:11](Cl)=[O:12].O>ClCCl>[OH:4][CH2:3][C:2]([NH:1][C:11](=[O:12])[C:10]1[C:14]([O:22][CH3:23])=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:9]=1[O:8][CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 19911980HCID 19911980, compound

Product 1

HCID 58167761HCID 58167761, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.7 ml (37.22 mmol) 2-amino-2-methyl-1-propanol in 42 ml dichloromethane under nitrogen at 0° C., was added dropwise a solution of 5 g (18.61 mmol) 2,6-dimethoxy-4-trifluoromethyl-benzoyl chloride in 12 ml dichloromethane. The temperature rose to 7° C. The mixture was stirred at room temperature for 4 hours. The mixture was poured onto 75 ml water. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 5.66 g (yield: 94.6%) of the title compound as a yellow solid. MS (m/e): 322.2 (M+H+).

Workup

  1. customrose to 7° C
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-806d1d8eafdb42488b7f5e6531a7e176
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

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