Water → HCID 58167761, compound

HRID 1950931Notes

Reaction equation

HRID 1950931 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-814cc227c59b4e1baa5d89db34b0176e
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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